Ethyl bromoacetate → Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

HRID 1270401노트

반응식

HRID 1270401 반응식
[H-].[Na+].Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]([N:13]1[C:17]2[C:18]([Br:22])=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[O:23])(=[O:12])[CH3:11]>>[C:10]([N:13]1[C:17]2[C:18]([Br:22])=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:14]1=[O:23])(=[O:12])[CH3:11]

참가 물질

4

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 184493611-Acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 86607788Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

실험 절차

Sodium hydride (353 mg of a 60% dispersion in mineral oil, 8.84 mmol) and ethyl bromoacetate (1.15 mL, 8.84 mmol) were added to a solution of 1-acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one from Step B (1.5 g, 5.89 mmol) in DMP (20 mL) at 0° C. After 4 h, the reaction mixture was quenched with brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2::EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=343 (M+1).

후처리

  1. customthe reaction mixture was quenched with brine
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

출처 및 근거

ORD 기록
ord-6238911933994ab18f1506a67714ae1b
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202251B2

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