Tetramethyl orthocarbonate → 4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole

HRID 613600ノート

反応式

HRID 613600 の反応式
[NH2:1][C:2]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].[C:18]([O:25][CH3:26])(OC)(OC)OC>C(O)(=O)C>[CH2:11]([O:10][C:9]1[C:2]2[N:1]=[C:18]([O:25][CH3:26])[N:4]([CH3:5])[C:3]=2[CH:6]=[CH:7][CH:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

4

反応物 2

HCID 74613Tetramethyl orthocarbonateHCID 104895412-amino-3-benzyloxy-N-methylaniline

生成物 1

HCID 107543614-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of 2-amino-3-benzyloxy-N-methylaniline (318.5 mg) in acetic acid (3.2 ml) was added tetramethyl orthocarbonate (223.0 μl) at ambient temperature, and the reaction mixture was stirred for 4 hours. The reaction mixture was concentrated in vacuo, and to the residue were added ethyl acetate and a saturated sodium bicarbonate solution. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was triturated with n-hexane-diisopropyl ether to give 4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole (273.3 mg) as a pale brown solid.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionto the residue were added ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with n-hexane-diisopropyl ether

出典と根拠

ORDレコード
ord-d7d1ba524b8c4248ad6b1cfa84899827
出典データセット
uspto-grants-1999_12
特許番号
US06008229

反応ノート

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