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

HRID 865043Notes

Reaction equation

HRID 865043 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aadde0cc1b864fab85aa3149055c2515
Source dataset
uspto-grants-1996_10
Patent number
US05565465

Reaction notes

Loading…