Aniline → N-phenyl-3-chloropropylsulfonamide

HRID 1060835ノート

反応式

HRID 1060835 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 dropwise added to a solution of aniline (0.5 ml, 8.23 mmol) in pyridine (5 ml) with cooling at −20° C. 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. From the intermediate 3j, the desired compound 4j (yield: 57%) was yielded as a pale yellow solid in a manner as described in Preparation 1. IR (CHCl3)cm−1: 3020, 1598, 1495, 1315, 1139. NMR (CDCl3) δ: 2.46-2.60 (2H, m, CH2), 3.34-3.42 (2H, m, CH2), 3.78 (2H, t, J=6.6 Hz, CH2), 7.10-7.40 (5H, m, C6H5).

後処理

  1. temperaturewith cooling at −20° C. 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-9b85565d639243438a8a1e2760581655
出典データセット
uspto-grants-2003_02
特許番号
US06525081B1

反応ノート

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