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

HRID 1871100노트

반응식

HRID 1871100 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0ecd894acb74a538546d69f0a9fe56c
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100284

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