1,1'-Carbonyldiimidazole → HCID 12926629, compound

HRID 1454012Notes

Reaction equation

HRID 1454012 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>C1COCC1>[OH:9][C:3]1[C:2]2[NH:1][C:10](=[O:11])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 5799372,3-Diaminophenol

Product 1

HCID 12926629HCID 12926629, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,3-diamino-phenol (50 mg; 0.4 mmol) and 1,1′-carbonyl-diimidazole (65 mg; 0.4 mmol) in THF (5 ml) was stirred overnight. The crude product was purified by chromatography and by washed with water, to give pure 4-hydroxy-1,3-dihydro-benzoimidazole-2-one (32 mg; 53%). 1H NMR (DMSO-d6): 10.42 and 10.31 (s each, 2H), 9.46 (s, 1H), 6.70 (t, J=8.0 Hz; 1H), 6.41 (dd, J=0.8, 8.2 Hz; 1H), 6.40 (d, J=8.0 Hz).

Workup

  1. customThe crude product was purified by chromatography
  2. washby washed with water

Sources & evidence

ORD record
ord-714b7f805bea4ed0a83f12551a382d86
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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