Acetyl chloride → HCID 21949762, compound

HRID 2114667Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% dispersion in oil, 684 mg, 17.1 mmol) was added to a stirred solution of acetyl chloride (1.21 ml, 17.1 mmol) and the pyrazole of Example 53 (4.00 g, 15.6 mmol) in N,N-dimethylformamide (20 ml) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour and then quenched by the addition of water (100 ml). The aqueous extracted was with ether (2×50 ml). The combined organic phases were washed with water (30 ml) and brine (30 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 pentane:ether (90:10, by volume) to provide the title compound (3.0 g) as a white solid, m.p. <60° C.

Workup

customat 0° C.
customquenched by the addition of water (100 ml)
extractionThe aqueous extracted
washThe combined organic phases were washed with water (30 ml) and brine (30 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 pentane:ether (90:10, by volume)

Sources & evidence

ORD record: ord-053f98a1712d4de4bd31b53941662a53
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435728B2

Reaction notes

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