Reaction of acetylenedicarboxaldehyde bis (diethyl acetal) with bis

Reaction of acetylenedicarboxaldehyde bis(diethyl acetal) with bis(azidomethyl)benzene. Sultan T. Abu-Orabi, and Robert E. Harmon. J. Chem. Eng. Data ...
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J. Chem. Eng. Data 1986, 3 1 , 379-380

9e were formed (Scheme I). l e gave 88 and 9e on heating the reaction mixture and 8e, 98, and 3e at room temperature. On the other hand, 9f, 6g, 81, and 31 were obtained from l g under hot condition; 2g and 31 were formed when the same reaction was performed at room temperature. l h gave 9h, whereas, at room temperature the reaction products were 2h, 31, in addition to 6h and 9h. I n the case of 11, 81 was the only product. 11 gave 3k, 8k, 81, 91, and 61 when the reaction mixture was heated for 3 h. Authentic samples of 2a, 8b, 6a, 38, 88, 31, 61, 31, 81, and 6h were prepared by the methods reported earlier (3). Experhnental Sectlon

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are given in Table I. Satisfactory C, H, and halogen analyses were obtained for ail the compounds. R o g W No. l a , 39729-11-8;l b , 35820-37-2;IC, 10372-55-1;Id, 22219-26-7;l e , 29976-68-9;l f , 102260-70-8; 10, 75227-44-0;lh, 22129-40-4;11, 2997670-3; 11, 43016-14-4 l k , 102260-69-5; 11, 75767-98-5;2a, 1214-47-7;2g, 16635-10-22h, 16635-13-5;3b, 121822-0;30,29976-645;3f, 10226-W 51,29978687;3k, 102260-60-6; Ba, 487-26-3;6g, 14166-166;8h, 102260-61-7;Be, 29976-76-9;81, 102260-62-8;8k, 102260-63-9;Ob, 102260-64-09c, 10226065-1;Or, 102260-66-2; 91, 102260473; gh, 72149-92-991, 102260-6W Me,SO, 67-68-5.

Llterature Clted

Melting points are uncorrected. Reaction mixtures were separated by column chromatography uslng silica gel and the purity was checked by thin-layer chromatography (TLC). R e a c t h of i'-Hydroxychalcone DlbromMs ( l a ) wlth Me,SO. (a) The chalcone dibromkle (la) in Me,SO (20 mL) was heated on a water bath for 3 h and the reaction mixture was allowed to cool to room temperature. I t was diluted with water and the precipitate was fibred off, washed with water, and dried. TLC showed six spots. By column chromatography 8b, 9c, 3b, 6a, and Sa were separated using petroleum ether, benzene, and other as eiuotropic solvents. (b) A mixture of the chalcone dibromide (la) and Me,SO (20 mL) was kept at room temperature for 5 days. I t was then worked up as described above to give 3b, 2a, and 6a. Similarly, the reactions of other chalcone dibromides (lb-1) with Me,SO were carried out and data of the reaction products

(I) Epsteln, W. W.; Sweat, F. W. Chem. Rev. 1987, 6 7 , 247. (2)Kornbium, N.; Powers, J. W.; Anderson, G. J.; Jones, W. J.; Larson, H. W.; Lhrand, 0.;Weaver, W. N. J . Am. Chem. Soc. 1957, 79, 6582. (3)Reddy, N. J.; Bokadia, M. M.; Sharma. T. C.; Donnelly, J. A. J . Org. Chem. 1981, 46, 838. (4) Feuresteln, W.; Kostanecki, St. Von. Chem. Ber. 1898, 3 7 , 715.

(5) ChCHsiungUn: Chlu-Tsudln; Chin Lung Yeh. J . Chem. Soc. (Tal@) 1887, 14 (l),9. (6) Sherma, T. c.; Pawar, S. R.; Reddy, N. J.; Donnelley, J. A. Indlen J . Chem. 1981, 208, 80. (7) Mahanthy, P.; Panda, S. P.; Sabata, B. K.; Raut, M. K. Indlen J . Chem. 1885, 3 , 121. (8) Ghlya, B. J.; Marathey, M. 0. J . Scl. Ind. Res. ( I n d h ) 1982,218, 28. (9) Mahai, H. S.; Venkataraman, K. J . Chem. Soc. 1935, 868. (IO)Fltzgerald, D. M.; OSuUhran. F. J.; Phllbln. E. M.; Wheeler, T. S. J . Chem. Soc. 1915, 860. (11)Wadodkar, P. N. IndlenJ. Chem. 1963, 1 . 183. (12)Kutumbey. K. R.; Marathey, M. Q. Chem. Ber. 1983, 9 6 , 913. Received for revlew January 28,1985. Accepted December 19,1985. We thank CSIR (New Delhi) for the award of a postdoctoralfellowshlp to N.J.R.

Reaction of Acetylenedicarboxaldehyde Bis( diethyl acetal) with Bis(azidomethyl)benzene Sultan 1. Abu-Orabi" Chemisby Department, Yarmouk University, Irbid, Jordan

Robert E. Harmon Chemistry Department, Western Michigan University, Kalamazoo, Michigan 4900 1 carboxaklehyde)tetrakis(ethyi acetals) (IIIa-c). (See Scheme

Three 1,l '-[phenylenebls(methylene)]blr( trlazole-4,5-dlcarboxaldehyde) tetrakb(ethy1 acetals) (II I a - c ) were synthesized by the condensatlon of acetylenedlcarboxaldehyde bh( dkthyl acetal) wlth 1,2-, and 1,3-, and 1,4-blr( azldomethy1)benzene.

I n continuation of our previous work on the condensation reaction of l-benzyi-1H-triazoie-4,5dicarboxaidehyde with cyclic ketones to form poiymethyiene-brklged benzyl triazola tropones ( l ) , we report in the present paper details on the preparation of the three bis(azidomethyi)benzenes (I Ia-c) and on their reactions with acetylenedicarboxaklehyde bls(dlethyi acetal) to give the phenylenebis(methyiene)bis(triazoie-4,5dl0021-9568/86/1731-0379$01.50/0

I .) Experlmental Sectlon Acetyienedicarboxakhyde b&(dlethyi acetal) was prepared from acetylene gas and triethyl orthoformate by the method described by Whol(2). Melting points were determined by using a ThomasHoover Unimelt instrument and are uncut~ected.The nuclear magnetic resonance spectra were taken on a Varian A-60 spectrometer using tetramethyisilane as an internal reference, and shifts (6) are reported in ppm. Reparathwt d the Bb ( 8 z ~ f h y f(118 ) -c ~ ). ~ To a solution of 13.0 g (0.2 mol) of sodium azide in 70 mL of water and 70 mL of methanol was added 17.5 g (0.1 mol) of the bis(chloromethy1)benzene. The mixture was heated in a bomb flask at 100 O C for 2 days. The methanol was removed on a rotary evaporator at diminished pressure. The residue was

0 1986 American Chemical Society

380 Journal of Chemical and Engineering Data, Vol. 31, No. 3, 1986

Table I. Physical Data and NMR Spectra of Prepared ComDoundsa ‘H NMR (CDCl3) mP, bP, yield, assigncompd OC OC/mmHg % ppm ment IIa 112-115/1 88 7.22 (aromatic. 4 H, 8 ) 4.26 (ArCH2-, 4 H, 8 ) 118-120/1.5 88 7.18 (aromatic, IIb 4 H, 8 ) 4.12 (ArCH,-, 4 H, 8 ) IIC (aromatic, 30-32 118-120/1 92 7.22 4 H, s) 4.21 (ArCH,-, 4 H, s) (aromatic, IIIa 160-164/0.001 73 7.18 4 H, 8 ) (+C-H, 5.99 2 H,8 ) 5.78 (ArCH,-, 4 H, s) 5.65 (X-H, 2 H, 8 ) 3.25-4.0 (-0CH2CH3, 16 H, m) 0.95-1.35 (-0CHZCH3, 24 H, m) IIIb (aromatic, 160-163/0.001 78 7.20 4 H, 9) (+C-H, 5.90 2 H, 8 ) 5.75 (ArCH2-, 4 H, s) (SC-H, 5.65 2 H, 8 ) 3.25-3.90 (-0CHZCH3, 16 H, m) 0.95-1.35 (-0CHzCH3, 24 H, m) 43 7.28 IIIc 70-71* (aromatic, 4 H, s) 5.89 (+C-H, 2 H, s) 5.73 (ArCH2-, 4 H, 8 ) 5.65 (+C-H, 2 H, s) 3.2-3.9 (-0CH2CH3, 16 H, m) 0.95-1.35 (-OCH,CHs, 24 H, m) “Elemental analyses (C, H, N) in agreement with theoretical values were obtained and submitted for review. *Analytical sample, recrystallized from petroleum ether. 1,2-Bis(azidomethyl)benzene (IIa). 1,3-Bis(azidomethyl)benzene(IIb). l,a-Bis(azidomethy1)benzene (IIc). 1,1’-[1,2-phenylenebis(methylene)]bis(triazole-4,5-dicarboxyaldehyde)tetrakis(ethy1 acetal) (IIIa). l,l’-[ 1,3phenylenebis(methylene)]bis(triazole-4,5-dicarboxaldehyde) tetrakis(ethy1 acetal) (IIIb). 1,1’-[1,4-phenylenebis(methylene)]bis(triazole-4,5-dicarboxyaldehyde)tetrakis(ethy1 acetal) (IIIc).

Scheme I

extracted three times with diethyl ether. The extracts were combined and drled over anhydrous CaCi,. The ether was

Recelved for review October 7. 1985. Accepted January 27. 1988. We express w graWtuda to YamMuk Unhrerslty and Westan Mlchtgan Unhrersity for their generous support of this research.

I

p

Q

2

evaporated, and the remaining ilquid was cautiously distilled to give the product. The boiling points, yields, and NMR data are listed in Table 1. Pmp8rathm of the 7,7’-(Phenyh?nebIs(methylene)@b(frlazole-4,s -dlcarboxahiohyde) Tetrakls(ethyl acetals ) ( I I I a - c ) . To a solution of 13.8 g (0.06 mol) of acetylenedicarboxaldehyde bls(dlethy1acetal) in 15 ml of absolute ethanol was added 5.64 g (0.03 mol) of the corresponding bis(azidomethyl)benzene. The resulting mixture was heated in a bomb flask at 90 O C for 30 h. The alcohol was removed under reduced pressure. The resulting product was either distilled or recrystallized from petroleum ether. The boiling points, melting points, yields, and NMR data are listed in Table I.

R.lllrtry No. Ia, 612-12-4; Ib, 6 2 6 1 6 4 ; IC, 623-25-6; I I a , 10243779-6; IIb, 102437-80-9; I I c , 102437-81-0; I I I a , 102437-82-1; I I I b , 102437-83-2; IIIC, 102535-03-5; (EtO)2CH~CH(OEt)2,3975-08-4.

Llterature Clted (1) AbuSkabl, S. T.; Harmon, R. E. J . Heterocycl. Chem.. in press. ( 2 ) Wohl, A. Chem. Ber. 1912, 45, 339.

Correction Henry’s Constants for Phenol over Its Diluted Aqueous Solution. Mahmoud F. Abd-ECBary,’ Mohamed F. Hamoda, Shigeharu Tanisho, and Noriaki Wakao, J. Chem. Eng. Data 1886, 31, 229-30.

The correct spelling of the second author’s name is Mohamed F. Hamoda, not Mahmoud F. Hamoda, as printed.