Trichloroacetyl chloride → HCID 67815290, compound
Reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]([C:33]([NH2:35])=O)=[N:15][N:16]([C:22]([CH3:32])([CH3:31])[CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[C:17]=2[O:18][CH2:19][O:20][CH3:21])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>C(Cl)Cl>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]([C:33]#[N:35])=[N:15][N:16]([C:22]([CH3:32])([CH3:31])[CH2:23][C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[C:17]=2[O:18][CH2:19][O:20][CH3:21])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
171 mg of 4-(4-hexylphenyl)-5-(methoxymethoxy)-1-(2-methyl-1-(p-tolyl)propan-2-yl)-1H-pyrazole-3-carboxamide was dissolved in 2 mL of methylene chloride and mixed with 0.3 mL (2 mmol) of triethylamine. The reaction solution was cooled to 0° C. in an ice bath, and after dropwise addition of 0.080 mL (0.72 mmol) of trichloroacetyl chloride at room temperature for 1.5 hours. After completion of the reaction, the reaction mixture was mixed with methylene chloride and washed with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give the desired product (crude yield 266 mg).
Workup
- customAfter completion of the reaction
- washwashed with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-65df71659f8d4cb180f0234434fa2b31
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658686B2
Reaction notes
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