New benzimidazoles

Feb 6, 1970 - New Thio Derivatives ofCarcinogenic Arylamines. IV.1 4-Acetamido-3-methylthiodiphenyl. T. Lloyd Fletcher, Carol-Axx Cole, Hsi-lvxg. Pax,...
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J o i ~ r n ( of ~ 1dlcdicintrl Chcmislry, 1 N 0 , Vol. 13, AVO../( 785

I

TAtiLI:.

I

Y

s

Y

Recrystn solvent

;\Ietliod

1

H

2

H H

H H

.1

3

4

I1

5

RIP, oc

Yield

L7a

Anal>ses

Forniula

EtOH

179-180

75

CzzHirNz

S

-4

H20 (HCI) EtOH

286-288 deca 310-312 dec

45 93

CijH1zXz0 HCI CijHizSzO. HC1

C, H , hC , H. Clb

H

,1

HrO

275-276 dec

87

CisHizNz02. HC1

e, H , CIC

I1

H

A

EtOII

231-232

30

N

G

11

11

A

Et011

183.&184.5

11

C. 11

I

I1

11

A

DRIF-II20

237-238

34

c , 11

sd

€1

I1

A

EtOH

258.5-260

82

N

Be

H

CHI

EtOH

168-169

84

e. €I

10

so*

€1

.1

.1mOH

281-282

55

S

11

c1

H

13

Xylene

145149

71

12

H

H

B

EtOH

219-220

52

NO?

I1

B

;\leOCH~CHjOH

261-262

65

CinHoCIL'J30?

c1

14

c1

H

B

E t 0 H-HzO

219 5 2 2 0 5 dec

71

Ci.HgC13Sz

c1

15

H

H

B

>I e 0 C H2C H ? 0H

23 2-23 3

80

Ci,HnBrN?

C, H , N , Br

16

H

H

B

EtOH

242-243 d e d

44

CnHloX?S

C, H , 1

17

Pi02

H

B

bIeOCH?CH*OH

287-291 dec

50

CuHsN30zS.HCI

CI, N, S'

18

c1

H

B

Toluene

201.5-202.5

51

CisHsCINzS

S, c 1

19h

H

H

EtOH

245.5-247.5 dec

70

CnHgBrXzS HBr

S

20'

c1

H

MeOCHzCH20H

298-299 dec

58

ClaHBBrClPizS. HBr

S

1;3

CisHsClaPit

c1 N , CI

HC1 salt. Base mp 193-194" from xylene (C, H, N). HCI salt. H: calcd, 4.80; found, 5.40, 5.35. CI: calcd, 13.00; found 13.49, 13.58. c HC1 salt. H : calcd, 4.54; found, 5.13, 5.40. Previously prepared by Dr. W. Wenner. e 3lethiodide mp 287288' dec (C, H, N, I). J M p 234-235' was reported by Kalle A.-G., German Patent 1,105,713; Chem. Abstr., 56, 8215 (1962). 0 C1: calcd, 11.52; found, 10.85. Ii HBr salt. Base mp 185-187.5' from EtOH-H2O (Br, N, S). 1 HBr salt. was then extracted 3 times with 200-ml portions of boiling HJO, a t which time it usually solidified, to remove unreacted starting materials. The residue was then crystallized from an organic solvent. N-Alkylation (1 and 9).-2-Styrylben~imidazole~ and 10% M excesses of KOH and PhCH2C1 were dissolved in EtOH and the solution refluxed for 2.5 hr. The precipitated KC1 was (4) R. Weidenhagen, Ber.. 69, 2263 (1936).

filtered and the filtrate diluted with HSO, and cooled, during which process 1 separated. Compound 9 was prepared from 8 by refluxing 1 hr with excess Me1 in EtOH in the presence of NaOH; the product separated from the hot reaction mixture. Quaternization of 9 was accomplished by refluxing in Me&O with an excess of MeI; the product separated as the reaction progressed. Bromination (19 and %O).-The Br-free precursors (16, 18) mere dissolved in glacial HOAc and an equimolar solution of