Water → 4-Chloro-6-aminobenzimidazolone

HRID 1074590

Reaction equation

HRID 1074590 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([Cl:14])[C:5]=1[NH2:6])([O-])=O.[Se].[OH2:16].[CH2:17](N(CC)CC)C>O1CCCC1>[Cl:14][C:7]1[C:5]2[C:4](=[N:1][C:17](=[O:16])[N:6]=2)[CH:10]=[C:9]([NH2:11])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 190526-Chloro-2,4-dinitroanilineHCID 6326970Selenium

Product 1

HCID 189704694-Chloro-6-aminobenzimidazoloneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Dinitro-6-chloroaniline 2.7 g (12.5 m moles), selenium 1.98 g (25.0 m moles), water 1.6 ml (89 m moles), triethylamine 5.0 g (50 m moles) and tetrahydrofuran 100 ml were placed in a 200-ml capacity autoclave, and stirred at a temperature of 80° C. for five hours under carbon monoxide of 20 Kg/cm2. The reaction mixture obtained was worked up in the same manner as in EXAMPLE 1, to provide 4-chloro-6 -aminobenzimidazolone in 84% yield.

Workup

  1. customThe reaction mixture obtained

Sources & evidence

ORD record
ord-e5adb9b5df6e4e2b89c34407576fa6c0
Source dataset
uspto-grants-1983_07
Patent number
US04393216

Linked notes

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