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
