Methanol → 5-Bromo-1,3-dihydro-2H-benzimidazol-2-one

HRID 2386782Notes

Reaction equation

HRID 2386782 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=1.CO.O>CN1C(=O)CCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[NH:20][C:1](=[O:2])[NH:21][C:16]=2[CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 122280605-Bromo-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
100 °C

Procedure

1,1′-Carbonyldiimidazole (2.1 g) in NMP (5 ml) was added to a solution of 4-bromo-o-phenylenediamine (CAS Reg. No. 1575-37-7, 2 g) in NMP (5 ml). The mixture was heated to 100° C. for 2 h and then allowed to cool to 60° C. MeOH (3 ml) was added, and the mixture was allowed to cool to room temperature. Water (50 ml) was added. The mixture was filtered. The residue was washed with isopropanol and then dried in vacuo to give the title compound (1.65 g) as a dark brown solid. MS (m/e, ISP neg. ion)=213.1 [M−H+].

Workup

  1. temperatureto cool to 60° C
  2. temperatureto cool to room temperature
  3. filtrationThe mixture was filtered
  4. washThe residue was washed with isopropanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0e6244d71b8141d889592a2c8326bc5f
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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