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Phenylmethanesulfonyl chloride → 2-(4-Chlorophenoxy-methyl)-2-benzylsulfonylamino-propionitrile

HRID 2221132
ノート
印刷プレビュー

反応式

HRID 2221132 の反応式
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([NH2:12])([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.[CH2:15]([S:22](Cl)(=[O:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:12][S:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])([CH3:11])[C:9]#[N:10])=[CH:13][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 116585482-Amino-3-(4-chlorophenoxy)-2-methylpropanenitrile

生成物 1

HCID 116247712-(4-Chlorophenoxy-methyl)-2-benzylsulfonylamino-propionitrile

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

suspension of 1-(4-chloro-phenoxy)-propan-2-one (3.7 g, 20 mmol), ammonium chloride (1.6 g, 29.2 mmol) and sodium cyanide (1.15 g, 23.3 mmol) in a solution of aqueous ammonia (100 ml, 28%) is stirred vigorously at room temperature for 20 hours. The aqueous phase is extracted repeatedly with ethyl acetate. The collected organic extracts are dried and the solvent is evaporated under reduced pressure to give the 2-(4-chlorophenoxy-methyl)-2-amino-propionitrile as a solid. c) A solution of 2-(4-chlorophenoxy-methyl)-2-amino-propionitrile (0.5 g, 2.4 mmol) and benzylsulfonyl chloride (0.5 g, 2.6 mmol) in pyridine (5 ml) is heated at +80° C. with stirring in the presence of DMAP (0.02 g) for about 16 hours. The reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate and the product is purified by flash chromatography (eluent: ethyl acetate/hexanes 1:3) to give the 2-(4-chlorophenoxy-methyl)-2-benzylsulfonylamino-propionitrile in form of a colorless solid, m.p. 120-121° C.

後処理

  1. washwashed with brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe product is purified by flash chromatography (eluent: ethyl acetate/hexanes 1:3)

出典と根拠

ORDレコード
ord-c524c7a8def844a08fe5861c4daf0625
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07368479B2

反応ノート

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