Water → N-[4-(pyrrolidin-1-ylsulfonyl)phenyl]acetamide

HRID 17828

반응식

HRID 17828 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)(=[O:8])[CH3:7].O>CC(C)=O>[N:1]1([S:16]([C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[CH:15][CH:14]=2)(=[O:18])=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 962WaterHCID 8481N-Acetylsulfanilyl chlorideHCID 31268Pyrrolidine

생성물 1

HCID 720658N-[4-(pyrrolidin-1-ylsulfonyl)phenyl]acetamide수율 46.4%

시약·촉매·용매 1

HCID 180Acetone용매2회

반응 조건

온도
0 °C

실험 절차

(prepared according to an analogous procedure described in U.S. Pat. No. 5,755,873) Step A: Pyrrolidine (16 ml, 0.1925 mol) was dissolved in acetone (40 ml) and cooled to 0° C.; 4-acetylaminobenzenesulfonyl chloride (15 g, 0.065 mol) was added over 10 min. Additional acetone (13 ml) was added and the mixture was heated at reflux for 2 h. After cooling to rt, the mixture was added to water (350 ml) and the resulting precipitate collected by filtration, the precipitate was washed with water until the washings were at pH 7. The solid was dried under vacuum to give 8.1 g of N-[4-(pyrrolidine-1-sulfonyl)phenyl]acetamide. Step B: The compound from step A (8.1 g) was suspended in water (37.5 ml) and treated with concentrated HCl (19 ml). The mixture was heated at reflux for 1 h. After cooling to rt, NH4OH (23 ml) was added with stirring. The resulting precipitate was collected by filtration and washed with water until the washings were pH 7. The solid was dried to give 6.0 g of 4-(pyrrolidine-1-sulfonyl)phenylamine. 1H NMR (DMSO) δ 7.40 (d, J=8.8 Hz, 2H), 6.62 (d, J=8.8 Hz, 2H), 6.02 (s, 2H), 3.03 (m, 4H), 1.61 (m, 4H).

후처리

  1. custom(prepared
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 h
  4. temperatureAfter cooling to rt
  5. filtrationthe resulting precipitate collected by filtration
  6. washthe precipitate was washed with water until the washings
  7. customThe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-61ecc42835e8437d855135e8766b0e63
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741318B2

연결된 노트

불러오는 중…