1,1'-Carbonyldiimidazole → Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

HRID 1675774ノート

反応式

HRID 1675774 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>C1COCC1>[O:21]=[C:20]1[N:8]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18449398Ethyl 4-[(2-aminophenyl)amino]benzoate

生成物 1

HCID 18449399Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

A mixture of ethyl 4-[(2-aminophenyl)amino]benzoate from Step B (442 mg, 1.72 mmol) and 1,1′-carbonyldiimidazole (652 mg, 4.02 mmol) in THF (10 mL) was heated at 75° C. for 3 h. The cooled mixture was partitioned between EtOAc (100 mL) and 10% aqueous citric acid (50 mL). The organic layer was washed with H2O (30 mL), then brine (30 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-95:5 to 75:25, to give the title compound. MS: m/z=283 (M+1).

後処理

  1. customThe cooled mixture was partitioned between EtOAc (100 mL) and 10% aqueous citric acid (50 mL)
  2. washThe organic layer was washed with H2O (30 mL)
  3. dry with materialbrine (30 mL), then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

出典と根拠

ORDレコード
ord-9f7cc548c3994d988b6488f08873ad46
出典データセット
uspto-grants-2011_08
特許番号
US08003792B2

反応ノート

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