Water → 5-amino-2H-1,3-benzodiazol-2-one

HRID 1074589Notes

Reaction equation

HRID 1074589 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[CH:6][C:7]=1[NH2:8].[Se].[OH2:13].[CH2:14](N(CC)CC)C>O1CCCC1>[NH2:9][C:4]1[CH:5]=[CH:6][C:7]2=[N:8][C:14](=[O:13])[N:1]=[C:2]2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 51117914-Nitro-1,2-phenylenediamineHCID 6326970Selenium

Product 1

HCID 152505475-amino-2H-1,3-benzodiazol-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Diaminonitrobenzene 1.91 g (12.5 m moles), selenium powder 0.99 g (12.5 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 three 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 5-aminobenzimidazolone 1.80 g (90.0% yield).

Workup

  1. customThe reaction mixture obtained

Sources & evidence

ORD record
ord-080c24b9fc444ba2bfeb783a5b6de35d
Source dataset
uspto-grants-1983_07
Patent number
US04393216

Reaction notes

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