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Chloroacetone → Methyl 4-[formyl-(2-oxopropyl)amino]-3-methoxybenzoate

HRID 71136
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HRID 71136 반응식
[CH:1]([NH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:23][C:24](=[O:26])[CH3:25].C(OCC)(=O)C>CN(C=O)C.[I-].[K+]>[CH:1]([N:3]([CH2:23][C:24](=[O:26])[CH3:25])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15])=[O:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6571Chloroacetone2회HCID 8857Ethyl AcetateHCID 10796Cesium carbonate2회HCID 23085082Methyl 4-formamido-3-methoxybenzoate

생성물 1

HCID 86602464Methyl 4-[formyl-(2-oxopropyl)amino]-3-methoxybenzoate

시약·촉매·용매 2

HCID 4875Potassium Iodide
촉매
HCID 6228Dimethylformamide용매

실험 절차

To a mixture of methyl 4-(formylamino)-3-methoxybenzoate (25.8 g), cesium carbonate (80.4 g) and potassium iodide (2.04 g) in DMF (115 mL) was added dropwise chloroacetone (19.6 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. Cesium carbonate (40.2 g) and chloroacetone (9.8 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Ice water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. To the aqueous layer was added ethyl acetate, and the organic layer was separated. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (32.6 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. customthe organic layer was separated
  3. additionTo the aqueous layer was added ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-e3d04af8db2a49d1a86c605a59b8f46e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822699B2

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