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

HRID 1675774노트

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HRID 1675774 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9f7cc548c3994d988b6488f08873ad46
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003792B2

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