Hydrochloric Acid → Propanamide, 3,3,3-trifluoro-N-(4-mercaptophenyl)-
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
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) were charged to a flask. Concentrated HCl (22.5 mL) was slowly added to keep the temperature below 30° C. The reaction was then heated to 50° C. for 17.5 h. The reaction mixture was reduced to 41 mL by vacuum distillation at 50° C. Cool the reaction to room temperature and H2O (51 mL) was added. The slurry was filtered and the filter cake was washed with H2O (3×35 mL). The solid was dried under vacuum to produce the desired compound (19.9 g, 58%).
Workup
- customthe temperature below 30° C
- distillationThe reaction mixture was reduced to 41 mL by vacuum distillation at 50° C
- temperatureCool
- customthe reaction to room temperature
- filtrationThe slurry was filtered
- washthe filter cake was washed with H2O (3×35 mL)
- customThe solid was dried under vacuum
Sources & evidence
- ORD record
- ord-7b196d406c564b1ba5d9844c10d81afc
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129399B2
Reaction notes
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