Hydrochloric Acid → HCID 67967980, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](OC(F)(F)F)[CH:5]=[CH:4][C:3]=1[NH2:13].C[Al](C)C.C[O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[CH:24][N:23]=1)=O.Cl>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:13][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[CH:24][N:23]=1)=[O:19]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
2-Chloro-4-trifluoromethoxy-phenylamine (2.0 g, 9.29 mmol) in toluene (50 mL) was added to trimethylaluminum (2.0 M 4.65 mL) then 5-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester 3 (1.1 g, 4.65 mol) was added and the mixture was heated to 80-90° C. for 2 h. The reaction was cooled down and 1N HCl solution (10 mL) was added to be acidic. Dichloromethane (100 mL) was then added and the organic phase was further washed with water (100 mL) and dried over sodium sulfate. The solvent was removed and the residue was mixed with ether (50 mL) and stirred for 0.5 h. The solid was filtered and dried to give 5-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid (2-chloro-phenyl)-amide 4 as a solid. Yield: 1.0 g, 71%.
Workup
- temperatureThe reaction was cooled down
- washthe organic phase was further washed with water (100 mL)
- dry with materialdried over sodium sulfate
- customThe solvent was removed
- additionthe residue was mixed with ether (50 mL)
- filtrationThe solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-746f7f786c024f4c9c14cdf73f04489c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096587B2
Reaction notes
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