1,1'-Carbonyldiimidazole → 4-(2,2-Dimethoxyethyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 730569Notes

Reaction equation

HRID 730569 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[NH2:12].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16]>>[CH3:14][O:13][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[C:6]2[NH:12][C:15](=[O:16])[NH:11][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 578350073-(2,2-Dimethoxyethyl)benzene-1,2-diamine

Product 1

HCID 578349714-(2,2-Dimethoxyethyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 38%

Procedure

3-(2,2-Dimethoxy-ethyl)-benzene-1,2-diamine (1.03 g, 5.26 mmol) was dissolved in dTHF and carbonyldiimidazole (935 mg, 5.77 mmol) added. The mixture was stirred at rt for 18 hours. The solvent was removed and the crude material chromatographed to afford 4-(2,2-dimethoxy-ethyl)-1,3-dihydro-benzoimidazol-2-one as a colorless solid (440 mg, 38%). 1H NMR (CDCl3) δ 3.03 (2H, d, J=5.2 Hz), 3.40 (6H, s), 4.58 (1H, t, J=5.2 Hz), 6.86-6.89 (m, 1H), 6.96-7.02 (m, 2H), 9.29 (br s, 1H), 10.28 (br s, 1H). MS: 221 (M−H)−.

Workup

  1. additionadded
  2. customThe solvent was removed
  3. customthe crude material chromatographed

Sources & evidence

ORD record
ord-96458dcbcc71431b963f33d4814c1cef
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

Loading…