Dimethylformamide → Ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetate

HRID 534816Notes

Reaction equation

Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][SH:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[S:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (5.0 g), ethyl thioglycolate (3.97 g), potassium carbonate (5.53 g), and N,N-dimethylformamide (150 mL) was stirred at 80° C. for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate) to provide the title compound (2.12 g, 28%) as an oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-999bf2ae987c468a98364e5d7f0d8ad4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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