Acetyl chloride → HCID 58838571, compound

HRID 1173149Notes

Reaction equation

HRID 1173149 reaction equation
[H-].[Na+].[F:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([CH3:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:15].[C:30](Cl)(=[O:32])[CH3:31].C(OC(=O)C)(=O)C>O1CCCC1.C(N(CC)CC)C.CO>[C:30]([N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([CH3:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:14]([C:5]1[C:6]([C:10]([F:13])([F:11])[F:12])=[N:7][N:8]([CH3:9])[C:4]=1[F:3])=[O:15])(=[O:32])[CH3:31]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 57435625HCID 57435625, compound

Product 1

HCID 58838571HCID 58838571, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

At room temperature, 56.0 mg (2.3 mmol) of sodium hydride are added to a solution of 300.0 mg (0.78 mmol) of 5-fluoro-1-methyl-3-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide in 10.0 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 min, and 366.6 mg (4.7 mmol) of acetyl chloride and 2.2 g (21.2 mmol) of acetic anhydride are added. After 16 h of heating under reflux, the reaction mixture is added to 100 ml of methanol and 3 ml of triethylamine, and the mixture is filtered and concentrated under reduced pressure. Recrystallization from cyclohexane gives 182 mg (54.7% of theory) of N-acetyl-5-fluoro-1-methyl-3-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide of log P (pH 2.3)=4.63.

Workup

  1. temperatureAfter 16 h of heating
  2. temperatureunder reflux
  3. filtrationthe mixture is filtered
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-13007ad0a381485db119d57a423d2ff7
Source dataset
uspto-grants-2010_11
Patent number
US07834045B2

Reaction notes

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