Hydrochloric Acid → Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)-

HRID 499103Notes

Reaction equation

HRID 499103 reaction equation
FC(F)(F)CC(=O)[S:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:19])[CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:8][CH:7]=1.CCO.Cl>O>[F:18][C:15]([F:16])([F:17])[CH2:14][C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([SH:5])=[CH:7][CH:8]=1)=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 57674935S-4-(3,3,3-trifluoropropanamido)phenyl 3,3,3-trifluoropropanethioate

Product 1

HCID 57674932Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)-Yield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

S-4-(3,3,3-trifluoropropanamido)phenyl 3,3,3-trifluoropropanethioate (44.8 g, 189 mmol) and EtOH (70 mL) are charged to a flask. Concentrated HCl (22.5 mL) is slowly added to keep the temp below 30° C. The reaction is then heated to 50° C. for 17.5 h. The reaction mixture is reduced to 41 mL by vacuum distillation at 50° C. Cool the reaction to room temperature and H2O (51 mL) is added. The slurry is filtered and the filter cake is washed with H2O (3×35 mL). The solid is dried under vacuum to produce the desired compound (19.9 g, 58%).

Workup

  1. customthe temp below 30° C
  2. distillationThe reaction mixture is reduced to 41 mL by vacuum distillation at 50° C
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationThe slurry is filtered
  6. washthe filter cake is washed with H2O (3×35 mL)
  7. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-f25828aa473d470fbd6a8b602d91f0df
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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