Ethyl Acetate → (+/-)-3-[(4-Bromo-2,6-dimethylphenyl)amino]-5-chloro-1-[1-(methoxymethyl)propyl]-2(1H)-pyrazinone

HRID 324290

Reaction equation

Cl[C:2]1[C:3](=[O:15])[N:4]([CH:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Br:16][C:17]1[CH:23]=[C:22]([CH3:24])[C:20]([NH2:21])=[C:19]([CH3:25])[CH:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(OCC)(=O)C>C1COCC1>[Br:16][C:17]1[CH:23]=[C:22]([CH3:24])[C:20]([NH:21][C:2]2[C:3](=[O:15])[N:4]([CH:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=2)=[C:19]([CH3:25])[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To (+/−)-3,5-dichloro-1-[1-(methoxymethyl)propyl]-2(1H)-pyrazinone (300 mg) and 4-bromo-2,6-dimethylaniline (238 mg) in THF (anhydrous, 9.4 mL) at 0° C. was added sodium bis(trimethylsilyl)amide (1.0 M/THF, 2.6 mL). The mixture was stirred at 0° C. for 10 minutes. Ethyl acetate (100 mL) was added and washed with water (25 mL) and brine (25 mL). The organic layer was dried over MgSO4 and concentrated and the crude product was chromatographed on silica gel using ethyl acetate/hexane (1:4) as eluent. The product was then crystallized from ethyl acetate/hexane to afford the title compound (419 mg). Elemental analysis calcd. for C17H21N3O2BrCl: C, 49.23; H, 5.10; N, 10.13. Found: C, 49.33; H, 5.05; N, 10.09.

Workup

washwashed with water (25 mL) and brine (25 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customthe crude product was chromatographed on silica gel
customThe product was then crystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-969329ba337f44918f532a4b56db4fc7
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218391B1

Linked notes

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