Hydrochloric Acid → HCID 59430800, compound
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.C([N:16]([CH2:19]C)[CH2:17][CH3:18])C.[OH-].[Na+].Cl.[N:24]1C=[CH:28][CH:27]=[CH:26][CH:25]=1>>[NH:16]1[C:17]2[CH2:18][CH2:28][CH2:27][CH2:26][C:25]=2[N:24]=[C:19]1[C:7]([C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1)=[O:8]Participants
Procedure
The compound of Reference example 44-1 (3.13 g, 25.6 mmol) and 4-(trifluoromethyl)benzoyl chloride (10.0 g, 47.9 mmol) were dissolve in pyridine (20 ml) and the solution was stirred at room temperature. Therein was dropped triethylamine (4.85 g, 47.9 mmol) and the mixture was stirred for 4 hours at 60° C. Thereto was added 4N aqueous sodium hydroxide solution (20 ml) and the mixture was stirred for 3 hours at room temperature. The reaction mixture was neutralized with 1N diluted hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue was recrystallized from toluene to give the subject compound (5.24 g, 70%).
Workup
- stirringthe mixture was stirred for 4 hours at 60° C
- stirringthe mixture was stirred for 3 hours at room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customThe solvent was removed in vacuo
- customthe residue was recrystallized from toluene
Sources & evidence
- ORD record
- ord-2d780447475346aa994e53dbe585c1d3
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781479B2
Reaction notes
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