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

HRID 1270401ノート

反応式

HRID 1270401 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6238911933994ab18f1506a67714ae1b
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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