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

HRID 17828ノート

反応式

HRID 17828 の反応式
[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

参加物

5

反応物 3

HCID 962WaterHCID 8481N-Acetylsulfanilyl chlorideHCID 31268Pyrrolidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
0 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-61ecc42835e8437d855135e8766b0e63
出典データセット
uspto-grants-2010_06
特許番号
US07741318B2

反応ノート

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