Water → 2-Chloro-5-(4-methoxy-benzoyl)-N-phenethyl-benzenesulfonamide

HRID 1810161노트

반응식

HRID 1810161 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18](Cl)(=[O:20])=[O:19].[CH2:22]([NH2:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18]([NH:30][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:20])=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 1001PhenethylamineHCID 8471TriethylamineHCID 581074452-Chloro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride

생성물 1

HCID 581074872-Chloro-5-(4-methoxy-benzoyl)-N-phenethyl-benzenesulfonamide수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Chloro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride (0.2 g, 5.79 mmol) is dissolved in methylene chloride (10 mL). Phenethylamine (0.077 g, 6.36 mmol) is added, followed by the addition of triethylamine (0.146 g, 14.5 mmol). The reaction mixture is stirred for 2 h at room temperature. Water is added, and the mixture extracted with methylene chloride. The solvent is removed and the mixture is purified by flash column chromatography, using 50% of ethyl acetate-hexane as an eluent. The product is obtained as a colorless oil (0.13 g, 52% yield). 1H NMR (CDCl3): δ 8.4 (m, 1H), 7.90 (m, 1H), 7.50 (d, J=8 Hz, 2H), 7.28 (m, 3H), 7.00 (d, J=8 Hz, 2H), 7.17 (m, 2H), 4.97 (m, 1H), 3.91 (s, 3H), 3.20 (m, 2H), 2.80 (m, 2H). Analytics calculated for C22H20ClNO4S: C, 61.46; H, 4.69; N, 3.26. Found: C, 61.20; H, 4.95; N, 3.10. MS (m/z): 430.0 (M+1).

후처리

  1. extractionthe mixture extracted with methylene chloride
  2. customThe solvent is removed
  3. customthe mixture is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-2df8346f45604d4789874910c685f6ee
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362063B2

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