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

HRID 1257164ノート

反応式

HRID 1257164 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-a7a97009dcae477cb0d038e7a5a5669e
出典データセット
uspto-grants-2013_06
特許番号
US08461179B1

反応ノート

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