c,
H Xa,R = H h, R = CH
(,
H
SI
I
C, H; ST1
II
H
(',
XITI E1
X1V
>;\'a. li.
n = A( K=H
Experimental Section ALelting pc~iritawere detei,mitietl i i i opeii capillary tubes O I L :I Alel-Temp apparatiih aiid are ~iiic(irrecied. Prwedrirea ii>etl t(ir 1 he preparat ioti ( i f iiew compoiiiidh are indicated by the appropriate reference; when c.hr~matogi,;tphy was reqiiired for the isola1 ioii [ i f piire materialb, as confirmed by thin layer chromatography, 1 he details are >-iinimarized. .U c8hromatographywa': c.oiidiirted o t i a syiithetiv magiiesia-.~iIic*a.gel adsorbent, The petroleiim rther itred rva. the fi,ac.tioti boiliiiy at 30-60". 1Yhei.e analyse:we itidicated (iiily t)y synibc~lsof the elemelit;, atialyt ica1 resrilt. were within rt0.4f; of the theoretiral valiies. 3-Phenyl-5-trifluoromethoxyanthranil(Va) w w prepared t i ) . -1 triflriorometh>-l ether'b with I'lieluted with petrolerim ether--C:I1 lIeyC:O-H20) with dificiilty : 20' IlsFaSO!) C, 11, 4. 3-Phenyl-5-trifluoromethylthioanthranil(Vb).---Phenyl t 1.if ~ l ~ l i f ' O ~ l esiilfide t h p l (i34.5 g, 0.194 mole) wt-nitrated as dew'ibeti previorisly.li' I )istillation of the criide prodiic,t i2S a ) with :I apinitiiiy-baiid c ~ r l i i r n i igave 4 T " , of R mist lire of 0- aiid p-nitrophenyl trifliiororner hyl siilfitle.. C'i~iideii*atioii( i f L>.:3 g of t hi? tiiistrii'e with PhCII2CX w:i< c,ffec.ted n-ith niethxrirdic. KO€i.L.q The prodiic,t, i-oliireci w i t h ertwi,, K W tli.-solvetl i n pet roleiini ethet,-CIlrC1:! (:3: 1) aiid chrc~ni:~togf'aphetl.The inatwin1 c l i i t ed by pet rolerim ether-CH1Clp to fiirtii.sh 7.:14 y ( X f ~ ;of) )-ellow ( l i z d from lIeO€I-€I?O had rnp 07-!)X". .1 nwl. IC14HsF,NOSI ('! FI, N, S. I he remainiiiy i i e w c~c~niporiiitl~ :ire giveii i i i Table 11. r ,
Acknowledgment.-:\ 1icro:mnlyses w r c fiunished :\[I-. I,. 13r:incoiie :md hi:: st,:iff.
clq.yHc?Hrl H
BuNHCONHS02
0 V
unlibely, yieldq uiider compimihle react ion coiidiiioii. :I iiiono~nlfonjlurea derivative (I7)of very siinilnr st i w ture to 11. We t w :it :i lo+ t o cxplnin the u k r v c d differenceh uiider n hat :ippcws t o be cxl reactioii cottditioii5. Compourid I1 IVRS dtvoid of hypoglycemic activity i t i the guinea pig hut showed a diuretic poteiiry in rat e-sentially fquivaleiit t o that of hydrochlorothi:izi(~(.. but with :t ~oniew\.hat, better Sa IC ratio. ('ompoiind 5' \VAS much less potent than I1 ai n diuretic. agelit. 4
Experimental Section'
Sulfonylureas Having Diuretic Activity
6-Chloro-3,4-dihydro-7-( N-butylcarbamoyl)sulfamyl-2H-l,2,4benzothiadiazine 1,l-Dioxide.-To H soliition of 10 0 g (0.0.LX mole) of R-rhlor1)-.2,4-dihydro-'i-s~ilfamoyl-%H-1,2,4-ben~cithi~/ m e 1,l-dioxide ( I ) 111 34 nil (0.0336 mole) of 1 S SaOH and 34 nil of X e X O at loo, wa\ added :; 32 g (0.0336 mole) of n-biiiyl ( 2 ) F. lioraer in " O r r a n i c Sillfur C~~niporinds." T-ol. I. S . I,b:,i., Pergamon Press Inc., Sen- Y o r k , S . I-.,1861. p 495. ( 3 ) We are indelitrit IO I l r . -1 Maaw and D r . 11. R'alz and tlieir statis. these lahoratories, fiir t l l r luological test rmults. For the diuretic a w a y , t titi procedure of V. 13. \VirAelliaiis, F. T. Hrennan, a n d G . I . S
