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

HRID 865041Notes

Reaction equation

HRID 865041 reaction equation
[OH:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[C:12]1([S:18]([C:21]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C>CC(N(C)C)=O>[C:12]1([S:18]([C:21]2[CH:22]=[CH:23][C:24]([NH:25][C:5]([C:2]3([OH:1])[CH2:4][CH2:3]3)=[O:7])=[CH:26][CH:27]=2)(=[O:19])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 5166664-(Phenylsulfonyl)anilineHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acid

Product 1

HCID 21480116N-[4-(Phenylsulfonyl)phenyl]-1-hydroxy-cyclopropylcarboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of 1-hydroxycyclopropanecaboxylic acid (0.66 g, 6.44 mmol) in dry dimethylacetamide (10 ml) was stirred under a nitrogen atmosphere at -15° C. Thionyl chloride (0.77 g, 6.44 mmol) was added and the resulting mixture was allowed to stir at -15° C. for 1 hour. 4-Phenylsulfonylaniline (1.0 g, 4.29 mmol) was then added and the reaction mixture was stirred at -15° 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 ice, extracted with ethyl acetate, and the combined ethyl acetate portions were washed with 1M HCl. After drying (MgSO4) the ethyl acetate was removed by evaporation to give a buff-colored solid. Crystallization of this material from ethyl acetate/hexane yielded the title tertiary carbinol, (0.82 g, 60%) as a white solid; mp=214.5°-216° C. 1H-NMR (250 MHz, d6 -DMSO): 0.98 (m, 2H, 2 CH2), 1.15 (m, 2H, CH2), 6.63 (s, 1H, OH), 7.65 (m, 3H, ArH), 7.95 (m, 6H, ArH), 10.29 (s, 1H, NH). MS (CI, CH4): 318(M+1, 100).

Workup

  1. stirringthe reaction mixture was stirred at -15° 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 ice
  5. extractionextracted with ethyl acetate
  6. washthe combined ethyl acetate portions were washed with 1M HCl
  7. dry with materialAfter drying (MgSO4) the ethyl acetate
  8. customwas removed by evaporation
  9. customto give a buff-colored solid
  10. customCrystallization of this material from ethyl acetate/hexane
  11. customyielded the title tertiary carbinol, (0.82 g, 60%) as a white solid

Sources & evidence

ORD record
ord-36adc7ba604e401a863f982f51eb30c0
Source dataset
uspto-grants-1996_10
Patent number
US05565465

Reaction notes

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