O-Phenylenediamine → 2-Hydroxy benzimidazole

HRID 1197839Notes

Reaction equation

HRID 1197839 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]1([NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19]>C1COCC1>[NH:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:20][C:1]1=[O:2]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 119852-Hydroxy benzimidazoleYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of 1,1'-carbonyldiimidazole (10.7 g) and THF (100 ml) was added to a mixture of 1,2-phenylenediamine (6.48 g) and THF (150 ml) which had been cooled to approximately 5° C. in an ice-water bath. The mixture was stirred at ambient temperature for 16 hours. The precipitate was filtered off giving 2,3-dihydrobenzimidazol-2-one (4.38 g, 55%), m.p. >290° C.

Workup

  1. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-260d98ea856447108476a67b7c9efbf2
Source dataset
uspto-grants-1994_01
Patent number
US05278177

Reaction notes

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