Hydrochloric Acid → N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500067Notes

Reaction equation

HRID 1500067 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:12]([C:13]([OH:15])=O)=[C:11]([C:16]([F:19])([F:18])[F:17])[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[N:9]1.N1C=CC=CC=1.[NH2:33][C:34]1[CH:35]=[CH:36][C:37]([Cl:43])=[C:38]([C:40](=[O:42])[CH3:41])[CH:39]=1.Cl>CN(C=O)C.ClCCl.C1COCC1>[C:40]([C:38]1[CH:39]=[C:34]([NH:33][C:13]([C:12]2[N:8]([CH3:7])[N:9]=[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:22])[F:23])[C:11]=2[C:16]([F:18])([F:17])[F:19])=[O:15])[CH:35]=[CH:36][C:37]=1[Cl:43])(=[O:42])[CH3:41]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 15019111-(5-amino-2-chlorophenyl)ethanoneHCID 866600921-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 89650518N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamideYield 80%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

Oxalyl chloride (0.65 ml, 0.95 g, 7.5 mmol, 1.5 eq.) followed by DMF (3 drops) were added to 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (1.56 g, 5.00 mmol) in dichloromethane (20 ml), and the mixture was heated to 40° C. After 9 h at 40° C., the mixture was concentrated under reduced pressure, THF (20 ml) and pyridine (0.8 ml, 0.8 g, 2.0 eq.) were added, followed by 1-(5-amino-2-chlorophenyl)ethanone (0.85 g, 5.00 mmol, 1.0 eq.) in THF (5 ml). The mixture was left at room temperature for 2 d. HCl N aq. solution) was added, the mixture was extracted with ethyl acetate and the extract was washed with HCl (1N aq. solution), NaOH ON aq. solution) and sat. aq. sodium chloride solution. The extract was dried over MgSO4 and, after concentration under reduced pressure, the product was purified by column chromatography on silica gel (hexane/ethyl acetate) to give N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (1.85 g, 80%).

Workup

  1. additionwere added
  2. waitThe mixture was left at room temperature for 2 d
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract was washed with HCl (1N aq. solution), NaOH ON aq. solution) and sat. aq. sodium chloride solution
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationafter concentration under reduced pressure
  7. customthe product was purified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-327a6421a2b54688a812cde98fc6974b
Source dataset
uspto-grants-2015_12
Patent number
US09204645B2

Reaction notes

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