XRWCOMPOUNDS
228.1
Some Quaternary Salts Containing Aryloxyethyl and Aryloxypropyl Groups A number of salts of the two types [p-CICl~H~zO( CH2)nN+Me2RIYr (p-CIC1?HleO)NCaHsBr KI have bem prepared by the following general procedure Thymol and P-chlorothymol, reacting as the sodium salts with ethylene and trimethylene bromohydrins. gave ether alcohols which were transformed into bromides by phosphorus tribroniidc in the usual manner and the bromides were allowed t o react with dimethylamine in methanol a t 120-125" The resulting tertiary amities on treatment with appropriate alkyl halides produced the quaternary S d h of type I As a variant chlororymoxyethyl bromide was allowed t o act on pyridine and %,4-dimethylthiazole, yielding the members of type 11. The quaternary salts were purified by crystallization from absolute alcohol with addition of ether or ethyl acetate.
VOl. 64
sults from the interaction of indium salt solutions with those of soluble salicylates. Basic Indium Salicylate Tri-hydrate.-To 2.0000 g. of anhydrous indium sulfate dissolved in 50 ml. of water was added 25 ml. of a solution containing 4.5553 g. of sodium salicylate (mole ratio of 1 to 3). The resulting finely divided white precipitate was removed tiy filtration, washed until sulfate and sodium free, and air dried by suction. The product consists of microcrystalline needles which are very slightly soluble in water, ethanol and methanol, insoluble in benzene and toluene, hut readily soluble in hot dilute acids. On ignition, the solid chars and is converted quantitatively to indium oxide. Prolonged drying at 110' yields the anhydrous compound. A n d . Calcd. for In(C7HsOs'hOH.3Hz0: In, 24.95. Found: In (by ignition), 24.83. Anhydrous Basic Indium Salicylate.-Two grams of the trihvdrate was dehydrated by boiling with absolute meth-
____-
Analyses,
---.
yo Found c
_ _ I _ _ -
Calcd.
K
Y
I I C1
c1 C1
I C1 c1
c1
tl
2 2 2 >
I
->
3 3 3 3
N-Pyridyl S-2,%Diniethylthiazolyl ' Xuclear C1 replaced by H.
Formula C 4c. [p-CIC,oHlzO(CH?),NCMe2RIY49.57 176 CisHzeONI 45.27 228 CiaH2sONCII (i5.95 194 C~iH290NCi2 6 0 . -19 210 CziH2aONCl( ti0 49 175 C21HnaONCls 46. ti5 229 CieHz70NClI 61 31 204 CzzHdNC1, 191 CzlH300NC1zBr 55 57 184-187 CzsH4z02NC1zBr 58.41
€1
M. p . ,
p-CICloHl~OCHtCHzRBr 55.05 119-120 C17H210NClBr 214 C17HzsONSCIBr 50.42
BURROUGHS WELLCOME AND CO., Ij. s. -4. EXPERIMENTAL RESEARCH LABORATORIES WALTERS. IDE ' h C K A H O E , NEWU O R K RICHARD BALTZLY JOHANNES S. BUCK RECEIVED MAY18, 1942 Basic Indium Salicylates Insoluble basic indium salicylate analogous to the basic indium salts reported for a nunher of organic acid\' re{ l ) Ekeley and ,lohiison. 'THIS J U I J X N A I , , 57, 773 11935).
7.22 ti.34
49.45 45.21
H
7.41 r i . 50 7.91)
7.63
tis. XK
77 6.77
G0.62 60.28 46.50 01.37 55.71
t i . 99
sx .fi7
(5.61 7. 13 (5.62 7.52
55.18 si).53
ti. 00 B . ( ).'3
ti.
6.fil 7.02 ti. 37 7 .ai; 3.72 5 . ;:i
( j .89
anol. The residue was washed successively with methanol and ether and dried for one hour at 110". In appearance and behavior it resembles the hydrate.
Anel. Calcd. for In(C,H50&0H: In, 28.27; salicylate, fi7.54. Found: In, 28.23, salicylate (bromate titration), G7.fi-l. NOYES CHEMICAL LABORATORY TJNIVERSITI' O F I L L I N O F
I'RDAXA,ILI.INOIS R F C E I I;L) ~
JUNE
THERALD MOELLER 29, 1942
