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

HRID 1270366ノート

反応式

HRID 1270366 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, which was of sufficient purity for use in the next step. 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-333e9b8dbfa34da49cf62192346dff4f
出典データセット
uspto-grants-2007_04
特許番号
US07202251B2

反応ノート

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