Dimethylformamide → HCID 23079533, compound

HRID 1365026Notes

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-59233803a15f4459b4eba047ced78677
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888487B2

Reaction notes

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