Water → N-(4-chloro-3-(cyanomethyl)-2-fluorophenyl)acetamide

HRID 1257164

반응식

HRID 1257164 반응식
CS(O[CH2:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]([NH:14][C:15](=[O:17])[CH3:16])[C:8]=1[F:18])(=O)=O.[C-:19]#[N:20].[Na+].O>CS(C)=O>[Cl:13][C:12]1[CH:11]=[CH:10][C:9]([NH:14][C:15](=[O:17])[CH3:16])=[C:8]([F:18])[C:7]=1[CH2:6][C:19]#[N:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 867136263-Acetamido-6-chloro-2-fluorobenzyl methanesulfonate

생성물 1

HCID 86713627N-(4-chloro-3-(cyanomethyl)-2-fluorophenyl)acetamide수율 78.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 3-acetamido-6-chloro-2-fluorobenzyl methanesulfonate (1.31 g, 3.54 mmol) in DMSO (10 mL) was treated with sodium cyanide (0.868 g, 17.72 mmol), stirred at RT overnight, treated with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-chloro-3-(cyanomethyl)-2-fluorophenyl)acetamide (630 mg, 78% yield) as a yellow solid. MS (ESI) m/z: 227.0 [M+H]+.

후처리

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (EtOAc/Hex)

출처 및 근거

ORD 기록
ord-a7a97009dcae477cb0d038e7a5a5669e
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461179B1

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