Sulfuric Acid → N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}acetamide

HRID 735912Notes

Reaction equation

HRID 735912 reaction equation
[OH:1]S(O)(=O)=O.[F:6][C:7]([F:19])([F:18])[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)([CH3:16])[CH3:15])=[CH:10][CH:9]=1.[CH3:20][C:21]#[N:22]>>[CH3:15][C:14]([NH:22][C:21](=[O:1])[CH3:20])([C:11]1[CH:12]=[CH:13][C:8]([C:7]([F:19])([F:18])[F:6])=[CH:9][CH:10]=1)[CH3:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342Acetonitrile2×HCID 27776172-(4-(Trifluoromethyl)phenyl)-2-propanol

Product 1

HCID 67185937N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}acetamideYield 90%

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution H2SO4 (2.68 g, 27.3 mmol) in CH3CN (91 mL) was added dropwise a solution of 2-(4-(trifluoromethyl)-phenyl)-2-propanol (1.86 g, 9.1 mmol) in CH3CN (9.1 mL). The resulting reaction mixture was stirred at 0° C. for 1 h then at rt for 23 h. The solvent was evaporated under vacuo and H2O was added (20 mL). The mixture was extracted with Et2O (2×50 mL) and the combined organic layers were washed with H2O (2×20 mL), an aqueous solution of NaOH (1N) (2×20 mL), dried over MgSO4, filtered and evaporated to give the title compound as white solid (2.00 g, 90%). 1H NMR (CDCl3, 300 MHz) δ 7.69 (d, J=8.3 Hz, 2H), 7.59 (d, J=8.3 Hz, 2H), 2.10 (s, 3H), 1.79 (s, 6H). HPLC (Condition A), Rt: 3.18 min (HPLC purity: 97.2%).

Workup

  1. customThe resulting reaction mixture
  2. waitat rt for 23 h
  3. customThe solvent was evaporated under vacuo and H2O
  4. additionwas added (20 mL)
  5. extractionThe mixture was extracted with Et2O (2×50 mL)
  6. washthe combined organic layers were washed with H2O (2×20 mL)
  7. dry with materialan aqueous solution of NaOH (1N) (2×20 mL), dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-bbc85e72880c4f699d92bba450bb8bb1
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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