Methane → N-[4-(Phenylsulfonyl)phenyl]-2-hydroxy-2-methylbutanamide

HRID 327178Notes

Reaction equation

HRID 327178 reaction equation
[OH:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3](O)=[O:4].S(Cl)(Cl)=O.[C:13]1([S:19]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C>CC(N(C)C)=O>[C:13]1([S:19]([C:22]2[CH:23]=[CH:24][C:25]([NH:26][C:3](=[O:4])[C:2]([OH:1])([CH3:8])[CH2:6][CH3:7])=[CH:27][CH:28]=2)(=[O:20])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 95433(+-)-2-Hydroxy-2-methylbutyric acidHCID 5166664-(Phenylsulfonyl)aniline

Product 1

HCID 21480148N-[4-(Phenylsulfonyl)phenyl]-2-hydroxy-2-methylbutanamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 2-hydroxy-2-methyl butyric 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 (0.89 g, 62.5%) as a colorless crystalline solid; mp=163.0°-165.0° C. 1H--NMR (250 MHz, d6 --DMSO): 0.82 (t, J=7Hz, 3H, CH3), 1.32 (s, 3H, CH3), 1.56 (m, J=7 Hz, 1H, CH2), 1.76 (m, J=7 Hz, 1H, CH2), 5.65 (s, 1H, OH), 7.64 (m, 3H, ArH), 7.91 (m, 4H, ArH, 8.01 (d, J=11.1 Hz, 2H, ArH), 9.98 (s, 1H, NH). MS (CI, CH4): 334(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 (0.89 g, 62.5%) as a colorless crystalline solid

Sources & evidence

ORD record
ord-34b0fe26a3f042dfbcfbccc1acb274f6
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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