Allylamine → Benzamide, 2-(2-propen-1-ylamino)-4-(trifluoromethyl)-
Reaction equation
F[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:21]([NH2:24])[CH:22]=[CH2:23].CC(N(C)C)=O>C(OCC)(=O)C>[CH2:21]([NH:24][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])[CH:22]=[CH2:23]Participants
6
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 2-fluoro-4-trifluoromethylbenzamide (5.60 g, 27.05 mmol.), K2CO3 (11.2 g, 81.16 mmol), allylamine (7.71 g, 135.26 mmol) and dimethylacetamide (50 mL) was heated at 140° C. for 18 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with a solution of aqueous saturated sodium bicarbonate (3×100 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to give the title compound (6.5 g, 98% yield) as a brown solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washwashed with a solution of aqueous saturated sodium bicarbonate (3×100 mL)
- dry with materialThe ethyl acetate layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-847867d6b2024ce88603f8040ff83d5c
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238702B2
Reaction notes
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