Water → Benzimidazol-2-one
Reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Se].O.[C]=O.[O:13]1CCC[CH2:14]1>C(N(CC)CC)C>[N:7]1[C:14](=[O:13])[N:8]=[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=12Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
o-Phenylenediamine 1.35 g (12.5 m moles), selenium powder 0.99 g (12.5 m moles), water 1.6 ml (89 m moles), triethylamine 5 g (50 m moles) and tetrahydrofuran 100 ml were placed in a 200-ml capacity autoclave, and the atmosphere therein was replaced by carbon monoxide of 20 Kg/cm2. The contents in the autoclave were heated to 80° C. and held at the temperature for 3 hours with stirring. Thereafter the reaction mixture was cooled to room temperature, and carbon monoxide was removed from the autoclave. The reaction mixture was taken out of the autoclave and worked up in the same manner as in EXAMPLE 1 to provide benzimidazolone 1.66 g (99.0% yield) of 95.6% purity.
Workup
- temperatureThereafter the reaction mixture was cooled to room temperature
- customcarbon monoxide was removed from the autoclave
Sources & evidence
- ORD record
- ord-4b0cfb6db46646239f2f4f823b9c2065
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04374250
Reaction notes
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