Dimethyldioxirane → 2-Oxo-3-(2-oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)propanal

HRID 656419Notes

Reaction equation

HRID 656419 reaction equation
N=[CH:2][C:3](=[O:21])[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:6]1=[O:20].CC1(C)O[O:24]1>CC(C)=O>[O:21]=[C:3]([CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:6]1=[O:20])[CH:2]=[O:24]

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 866322931-(3-Imino-2-oxopropyl)-3-pyridin-2-yl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 574361812-Oxo-3-(2-oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)propanal

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-(3-imino-2-oxopropyl)-3-pyridin-2-yl-1,3-dihydro-2H-benzimidazol-2-one from Step A (54 mg, 0.19 mmol) in acetone (2 mL) at 0° C. was added a solution of dimethyldioxirane (0.02 M in acetone, 9.6 mL, 0.19 mmol). The reaction mixture was stirred for 90 min then concentrated in vacuo to give the title compound in sufficient purity for use in the next step.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-1ffb6a63911c4ee8aa1813e7260f42c5
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

Loading…