Dimethylformamide → HCID 23079533, compound

HRID 2102316Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:11]([CH:22]([CH3:24])[CH3:23])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:34]=[O:35]>>[CH2:1]([O:8][C:9]1[C:13]([CH:34]=[O:35])=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[N:11]([CH:22]([CH3:24])[CH3:23])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 230795283-(Benzyloxy)-5-(4-methoxyphenyl)-1-(propan-2-yl)-1H-pyrazole

Product 1

HCID 23079533HCID 23079533, compound

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-benzyloxy-1-isopropyl-5-(4-methoxyphenyl)-1H-pyrazole (0.40 g) in N,N-dimethylformamide (1.5 mL) was added phosphorus oxychloride (0.23 g) at 80° C. and the mixture was stirred at 80° C. for 1 hour. After cooling to room temperature, a sodium hydroxide aqueous solution (1 mol/L, 5 mL) was added to the reaction mixture and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give the title compound (0.42 g).

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with diethyl ether
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-7de6474a3abf441ca25788e1c319f40b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576063B2

Reaction notes

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