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

HRID 730569ノート

反応式

HRID 730569 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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)−.

後処理

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

出典と根拠

ORDレコード
ord-96458dcbcc71431b963f33d4814c1cef
出典データセット
uspto-grants-2009_09
特許番号
US07582760B2

反応ノート

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