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

HRID 327179노트

반응식

HRID 327179 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
-10 °C

실험 절차

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, 6 H, 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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0de070a26474bf59a176abd2a1cdc6f
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272163

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