O-Phenylenediamine → Benzimidazol-2-one

HRID 2301070Notes

Reaction equation

HRID 2301070 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C1C[O:12][CH2:11]C1>>[N:7]1[C:11](=[O:12])[N:8]=[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=12

Participants

3

Reactant 2

HCID 7243O-PhenylenediamineHCID 8028Tetrahydrofuran2×

Product 1

HCID 162542Benzimidazol-2-one

Procedure

A solution of phenylene diamine 6.48 g in dry THF (150 ml) was cooled to 5° C. A suspension of 1,1-carbonyldiimidazole (10.7 g) in THF (100 ml) was added to this solution over 15 minutes keeping the temperature below 10° C. The mixture was stirred for 16 hours and the resultant solid was collected and dried to give the title compound (4.5 g); NMR: 6.9 (s, 4H), 10.5 (s, 2H); MS (ESP−): 135 (M+H)+.

Workup

  1. additionwas added to this solution over 15 minutes
  2. customthe temperature below 10° C
  3. customthe resultant solid was collected
  4. customdried

Sources & evidence

ORD record
ord-5e4e0d2202ad4b29b4f611df280d68f9
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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