Ethanol → ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate

HRID 1528541

Reaction equation

HRID 1528541 reaction equation
Cl.[NH:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:3].C(N(CC)CC)C.C(O)C.[Cl:20][C:21](Cl)=[CH:22][C:23](=O)[C:24]([F:27])([F:26])[F:25]>ClCCl.CN(C)C=O>[Cl:20][C:21]1[N:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:3]=[C:23]([C:24]([F:27])([F:26])[F:25])[CH:22]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 155483241,1,1-Trifluoro-4,4-dichloro-3-buten-2-one

Product 1

HCID 66016896ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl hydrazinoacetate hydrochloride (2.8 g, 18.1 mmol) and triethylamine (9.2 g, 91 mmol) in a solution of ethanol (20 mL) and N,N-dimethylformamide (1 mL), a solution of crude 4,4-dichloro-1,1,1-trifluoro-3-buten-2-one in dichloromethane (20 mL) was added dropwise while keeping the temperature of the reaction mixture below 10° C. After stirring a further 2 h at below 10° C., the reaction mixture was concentrated under reduced pressure. The residue was diluted with diethyl ether, and the mixture was filtered. The resulting filtrate was concentrated to give 4.34 g of the title compound as a solid. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. customthe temperature of the reaction mixture below 10° C
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with diethyl ether
  4. filtrationthe mixture was filtered
  5. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-3a804372e6aa4a4f8aa7cbb7c7edb4f8
Source dataset
uspto-grants-2015_07
Patent number
US09090604B2

Linked notes

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