Pyridine → N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzamide
Reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9](O)[C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][CH:9]([NH:8][C:6](=[O:7])[C:5]1[CH:15]=[CH:16][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:10]([F:13])([F:12])[F:11]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A stirred solution of Example 1A (3.48 g, 15.0 mmol) in CH2Cl2 (60 mL) at 0° C. was treated with pyridine (1.20 mL). The reaction mixture was treated dropwise with thionyl chloride (1.10 mL, 15.0 mmol), and the reaction flask was equipped with a calcium chloride drying tube. The reaction mixture was stirred at 0° C. for 4 hours, the cooling bath was removed, and the solution was stirred at ambient temperature for an additional 12 hours. Concentration of the reaction mixture provided a white solid which was triturated with diethyl ether (2×200 mL) to provide 2.40 g of the desired product as a white solid.
Workup
- customthe reaction flask was equipped with a calcium chloride drying tube
- customthe cooling bath was removed
- stirringthe solution was stirred at ambient temperature for an additional 12 hours
- customConcentration of the reaction mixture provided a white solid which
- customwas triturated with diethyl ether (2×200 mL)
Sources & evidence
- ORD record
- ord-d28284691f8040318f5a67ad89dcfc2e
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06645968B2
Reaction notes
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