Water → HCID 19094274, compound

HRID 487191Notes

Reaction equation

HRID 487191 reaction equation
Cl.[CH2:2]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:9]2[C:19]([CH2:23]Cl)=[CH:20][CH:21]=[CH:22][C:8]=2[N:7]=1)[CH2:3][CH2:4][CH3:5].[C-:25]#[N:26].[Na+].O.[OH-].[NH4+]>CS(C)=O>[CH2:2]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:9]2[C:19]([CH2:23][C:25]#[N:26])=[CH:20][CH:21]=[CH:22][C:8]=2[N:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 131718349HCID 131718349, compound

Product 1

HCID 19094274HCID 19094274, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-n-butyl-7-chloromethyl-1-(2-chlorophenyl)methyl-1H-benzimidazole, hydrochloride (1 g, 2.6 mmol) in dimethylsulfoxide (10 mL) was treated with sodium cyanide (153 mg, 3.12 mmol). The solid slowly went into solution, and after stirring for 3 hours at 25° C., the reaction was poured into water, some ammonium hydroxide solution was added and the resulting white precipitate was isolated to give 0.77 g of crude product; mp 122°-124° C. Crystallization from methylene chloride/hexane provided 0.68 g (84% of 2-n-butyl-1-(2-chlorophenyl)methyl-7-cyanomethyl-1H-benzimidazole; mp 124°-125° C.

Workup

  1. customthe resulting white precipitate was isolated
  2. customto give 0.77 g of crude product
  3. customCrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-0fa7829aae624232b762801a70d52605
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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