Dimethylformamide → 2,6-Dichloro-5-fluoronicotinamide
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.C[N:18](C)C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 72 °C
Procedure
To a suspension of 10 g of 2,6-dichloro-5-fluoronicotinic acid in 30 mL of toluene, 8.5 g of thionyl chloride and 0.10 mL of N,N-dimethylformamide were added, and the mixture was stirred at 72° C. for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The resultant residue was dropped to 30 mL of 25% ammonium water at −20° C. The temperature was increased to 5 C.°, and the mixture was stirred for 30 minutes. The solid was filtered off to obtain 9.9 g of 2,6-dichloro-5-fluoronicotinamide as a white solid.
Workup
- additionwere added
- temperatureThe reaction mixture was cooled to room temperature
- distillationthe solvent was distilled off under reduced pressure
- additionThe resultant residue was dropped to 30 mL of 25% ammonium water at −20° C
- temperatureThe temperature was increased to 5 C.°
- stirringthe mixture was stirred for 30 minutes
- filtrationThe solid was filtered off
Sources & evidence
- ORD record
- ord-9d88fa9534da41fba2bada2511e4ee59
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367831B2
Reaction notes
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