Aniline → N-phenyl-3-chloropropylsulfonamide

HRID 36878ノート

反応式

HRID 36878 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1>[C:10]1([NH:9][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 6115AnilineHCID 154103-Chloropropanesulphonyl chloride

生成物 1

HCID 10014230N-phenyl-3-chloropropylsulfonamide収率 88%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-Chloropropylsulfonyl chloride 1 (1.456 g,8.23 mmol) was added dropwise to a solution of aniline (0.5 ml, 8.23 mmol) in pyridine (5 ml) with cooling at -20° to -30° C. over about 5 minutes. After the completion of the addition, the reaction mixture was stirred for another 45 minutes at room temperature. The reaction mixture was concentrated in vacuo and the residue was subjected to column chromatography on silica gel. From the fraction eluted with a mixture of ethyl acetate/n-hexane (1:2), 1.683 g (88%) of N-phenyl-3-chloropropylsulfonamide (intermediate 3j) was obtained as a yellow oil, which, when treated in a manner similar to that described in Preparation 1, gave the objective compound 4j as a pale yellow solid (yield 57%).

後処理

  1. temperaturewith cooling at -20° to -30° C. over about 5 minutes
  2. additionAfter the completion of the addition
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washFrom the fraction eluted with a mixture of ethyl acetate/n-hexane (1:2)

出典と根拠

ORDレコード
ord-755c19f4d4554402bcc4edcb827978e2
出典データセット
uspto-grants-1995_05
特許番号
US05418230

反応ノート

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