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

HRID 2239305ノート

反応式

HRID 2239305 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-7c690e24aec949af9893321babf744d2
出典データセット
uspto-grants-2010_05
特許番号
US07723321B2

反応ノート

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