Methanol → Methyl 4-(Benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylate

HRID 2239305노트

반응식

HRID 2239305 반응식
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:19]([OH:21])=[O:20])[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.S(Cl)(Cl)=O.[CH3:26]O>C(OCC)(=O)C>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:19]([O:21][CH3:26])=[O:20])[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 685745314-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

생성물 1

HCID 68577093Methyl 4-(Benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-methyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxylic acid (10.0 g, 35.4 mmol, STEP 4 in Example 1), and thionyl chloride (5.2 mL, 7.1 mmol) in methanol (300 mL) was stirred at 80° C. for 3 hours. The mixture was diluted with ethyl acetate, and washed with saturated ammonium chloride aqueous solution. The organic layer was dried over magnesium sulfate, and concentrated in vacuum. The residue was diluted with methanol, filtered to remove the precipitate, and the filtrate was concentrated in vacuum. The resulted solid was washed with dichloromethane to give the title compound as a brown solid (29.8 g, crude), which was used in the next step without further purification. MS (ESI) m/z: 297 (M+H)+, 295 (M−H)−.

후처리

  1. washwashed with saturated ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuum
  4. additionThe residue was diluted with methanol
  5. filtrationfiltered
  6. customto remove the precipitate
  7. concentrationthe filtrate was concentrated in vacuum
  8. washThe resulted solid was washed with dichloromethane

출처 및 근거

ORD 기록
ord-7c690e24aec949af9893321babf744d2
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723321B2

반응 노트

불러오는 중…