1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-chloro-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[Cl:13][C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[Cl:13][C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[OH:12])=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 1.77 g of 2-amino-4-(trifluoromethyl)phenol, 1.58 g of 3-chloroisonicotinic acid and 15 ml of pyridine, 2.70 g of WSC was added and stirred while heating at 60° C. for four hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was washed with a mixture solvent of tert-butyl methyl ether and hexane to give 1.80 g of 3-chloro-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide.
Workup
- additionwas added
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- additionWater was added to the residue
- extractionfollowed by extraction with ethyl acetate twice
- washThe combined organic layers were washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- washThe residue was washed with a mixture solvent of tert-butyl methyl ether and hexane
Sources & evidence
- ORD record
- ord-026708f6772b44a2b56866b8b7a41b4c
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324387B2
Reaction notes
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