Methane → N-[4-(Phenylsulfonyl)phenyl]-1-hydroxy-cyclopentanecarboxamide

HRID 865741ノート

反応式

HRID 865741 の反応式
[OH:1][C:2]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O.[C:14]1([S:20]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C>CC(N(C)C)=O>[C:14]1([S:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:27][C:7]([C:2]3([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:9])=[CH:28][CH:29]=2)(=[O:21])=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 1171771-Hydroxycyclopentanecarboxylic acidHCID 5166664-(Phenylsulfonyl)aniline

生成物 1

HCID 21480133N-[4-(Phenylsulfonyl)phenyl]-1-hydroxy-cyclopentanecarboxamide

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
-10 °C

実験手順

A solution of 1-hydroxycyclopentanecarboxylic acid (0.76 g, 6.4 mmol) in dry dimethylacetamide (15 ml) was stirred under a nitrogen atmosphere at -10° C. Thionyl chloride (0.76 g, 6.4 mmol) was added and the resulting mixture was allowed to stir at -10° C. for 1 hour. 4-Phenylsulfonylaniline (1.0 g, 4.29 mmol) was then added and the reaction mixture was stirred at -10° C. for a further 15 mins. The solution was then allowed to warm to room temperature where it was stirred overnight. The reaction mixture was poured onto water, extracted with ethyl acetate, and the combined ethyl acetate portions were washed with water, and brine. After drying (Na2SO4) the ethyl acetate was removed by evaporation. Crystallization from ethyl acetate/hexane yielded the title tertiary carbinol (0.70 g, 47%) as a white solid; mp=214.0°-216.0° C. 1H-NMR (300 MHz, d6 -DMSO): 1.73 (m, 6H, CH2), 1.97 (m, 2H, CH2), 5.67 (s, 1H, OH), 7.64 (m, 3H, ArH), 7.94 (m, 6H, ArH), 10.13 (s, 1H, NH). MS (CI, CH4): 346(M+1, 100).

後処理

  1. stirringthe reaction mixture was stirred at -10° C. for a further 15 mins
  2. temperatureto warm to room temperature where it
  3. stirringwas stirred overnight
  4. additionThe reaction mixture was poured onto water
  5. extractionextracted with ethyl acetate
  6. washthe combined ethyl acetate portions were washed with water, and brine
  7. dry with materialAfter drying (Na2SO4) the ethyl acetate
  8. customwas removed by evaporation
  9. customCrystallization from ethyl acetate/hexane
  10. customyielded the title tertiary carbinol (0.70 g, 47%) as a white solid

出典と根拠

ORDレコード
ord-6419fed8e348428199bcbf5de0e2edbb
出典データセット
uspto-grants-1996_10
特許番号
US05567735

反応ノート

読み込み中…