Dimethylformamide → HCID 22054420, compound

HRID 1829721Notes

Reaction equation

[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.CN([CH:29]=[O:30])C>O.ClCCl.[OH-].[Na+]>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[C:12]([CH3:13])=[C:11]([CH:29]=[O:30])[C:10]([CH3:14])=[N:9]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a hot solution of 1-(diphenylmethyl)-3,5-dimethyl-(1H)-pyrazole (25.0 g) in DMF (22 ml) was added phosphoryl chloride (8.87 ml) dropwise with stirring under nitrogen and the resulting mixture heated at 100° C. for 3 hr. It was cooled, diluted with water and dichloromethane and basified with 50% sodium hydroxide with ice/water cooling. It was extracted with dichloromethane, the organic extracts washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ethyl acetate/i-hexane (1:19) followed by ethyl acetate to give the sub-title compound as a solid (12.61 g).

Workup

temperatureIt was cooled
extractionIt was extracted with dichloromethane
washthe organic extracts washed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified by column chromatography over silica
washeluting with ethyl acetate/i-hexane (1:19)

Sources & evidence

ORD record: ord-c0a24c7dda2b41cd84792e7a139a5de7
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064126B2

Reaction notes

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