1,1-Dimethylethyl N-(4-chloro-2-nitrophenyl)carbamate → 5-Chloro-2-chloromethyl-1-(2-methanesulfonyl-ethyl)-1H-benzoimidazole

HRID 1500856Notes

Reaction equation

HRID 1500856 reaction equation
C(OC(=O)NC1C=CC(Cl)=CC=1[N+]([O-])=O)(C)(C)C.[CH3:19][S:20](C1C2C(=CC=CC=2)NC=1)(=[O:22])=[O:21].[Cl:32][C:33]1[CH:50]=[CH:49][C:36]2[N:37]([CH2:42][CH2:43]CS(C)(=O)=O)[C:38]([CH2:40][Cl:41])=[N:39][C:35]=2[CH:34]=1>>[Cl:32][C:33]1[CH:50]=[CH:49][C:36]2[N:37]([CH2:42][CH2:43][S:20]([CH3:19])(=[O:22])=[O:21])[C:38]([CH2:40][Cl:41])=[N:39][C:35]=2[CH:34]=1

Participants

4

Reactant 3

HCID 539801451,1-Dimethylethyl N-(4-chloro-2-nitrophenyl)carbamateHCID 618081805-Chloro-2-(chloromethyl)-1-[3-(methylsulfonyl)propyl]-1H-benzimidazoleHCID 867677903-methanesulfonyl-1H-indole

Product 1

HCID 549351335-Chloro-2-chloromethyl-1-(2-methanesulfonyl-ethyl)-1H-benzoimidazole

Procedure

5-Chloro-2-chloromethyl-1-(2-methanesulfonyl-ethyl)-1H-benzoimidazole was prepared in analogy to Example 1-2 by using (4-chloro-2-nitro-phenyl)-carbamic acid tert-butyl ester as starting material instead of 3-(methylsulfonyl)-1H-indole and 5-chloro-2-(chloromethyl)-1-(3-(methylsulfonyl)propyl)-1H-benzo[d]imidazole. MS obsd. (ESI+) [(M+H)+] 308.1.

Sources & evidence

ORD record
ord-677e7ffdf04c44e39ae96641fd5400eb
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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