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4-Nitrobenzenesulfonyl chloride → (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-nitrobenzenesulfonamide

HRID 2302084
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HRID 2302084 반응식
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH:8]([NH2:11])[CH2:9][CH3:10].C(N(CC)CC)C.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20]>C(Cl)Cl>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:11][S:28]([C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:27][CH:26]=1)(=[O:29])=[O:30])[CH2:9][CH3:10]
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참가 물질

5

반응물 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 149997103-Chloro-2-(2-aminobutyl)thiophene

생성물 1

HCID 12070688(R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-nitrobenzenesulfonamide수율 95.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Six grams of 3-chloro-2-(2-aminobutyl)thiophene is dissolved in 10 ml of methylene chloride in a 3-neck round bottomed flask blanketed with an inert atmosphere at 0° C. Triethylamine (6.6 ml) is added in one portion followed by 7.8 g of 4-nitrobenzenesulfonyl chloride which had been previously dissolved in 10 ml of methylene chloride. After stirring for 1 hour at ambient temperature, the methylene chloride is removed under vacuum and 40 ml of methanol is added with warming to dissolve all solids. The resulting solution is poured into cold water, agitated for 30 minutes, filtered and washed with cold water, and the isolated material is dried in a vacuum oven to provide (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-nitrobenzenesulfonamide (11.3 g) as a tan solid. MS: m/z (E1, 70EV) 375(10%). 1H NMR (200 MHz; CDCl3): δ 0.95 (3H, t, CH3), 1.7 (2H, m, CH2), 2.85 (2H, m, CH2), 3.5 (1H, m, CH), 6.65 (1H, d, CH), 7.0 (1H, d, CH), 7.9 (2H, d, Ph), 8.2 (2H, d, Ph).

후처리

  1. customblanketed with an inert atmosphere at 0° C
  2. customthe methylene chloride is removed under vacuum and 40 ml of methanol
  3. additionis added
  4. temperaturewith warming
  5. dissolutionto dissolve all solids
  6. additionThe resulting solution is poured into cold water
  7. stirringagitated for 30 minutes
  8. filtrationfiltered
  9. washwashed with cold water
  10. customthe isolated material is dried in a vacuum oven

출처 및 근거

ORD 기록
ord-83c682dc9ee741ca9976491500542203
출처 데이터셋
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06429315B1

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