Aniline → N-phenyl-3-chloropropylsulfonamide

HRID 352029노트

반응식

HRID 352029 반응식
[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

참가 물질

4

반응물 2

HCID 6115AnilineHCID 154103-Chloropropanesulphonyl chloride

생성물 1

HCID 10014230N-phenyl-3-chloropropylsulfonamide수율 88%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f455bbb7fad44d5fa7cda416de57713a
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743923B2

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