Acetyl chloride → HCID 21949902, compound

HRID 2114668Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% dispersion in oil, 840 mg, 21.0 mmol) was added to a stirred solution of acetyl chloride (1.50 ml, 21.0 mmol) and the pyrazole of Example 76 (4.80 g, 19.4 mmol) in N,N-dimethylformamide (20 ml) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 15 minutes and then quenched by the addition of water (200 ml). The reaction mixture was extracted with ethyl acetate (3×120 ml). The combined organic phases were washed with water (50 ml) and brine (50 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a yellow solid. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane to provide the title compound (5.00 g) as a white solid, m.p. <60° C.

Workup

customat 0° C.
customquenched by the addition of water (200 ml)
extractionThe reaction mixture was extracted with ethyl acetate (3×120 ml)
washThe combined organic phases were washed with water (50 ml) and brine (50 ml)
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto leave a yellow solid
customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record: ord-f090a9e76d5c43a4b4ad775c96245d18
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435728B2

Reaction notes

Loading…