Sodium hydride → 4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-oxazol-4-yl]benzonitrile

HRID 1436441Notes

Reaction equation

[CH3:1][C:2]1([CH3:8])[CH2:6][O:5][C:4](=[O:7])[NH:3]1.[H-].[Na+].I[C:12]1[O:13][CH:14]=[C:15]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[N:16]=1>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:8])[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:12]1[O:13][CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=2)[N:16]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A 5 mL flask was charged with 4,4-dimethyl-oxazolidin-2-one (1.0 g, 8.7 mmol) and sodium hydride (60% wt suspension in mineral oil) (40 mg, 1.2 mmol) was added and the mixture was stirred for 20 min. 4-(2-Iodo-1,3-oxazol-4-yl)benzonitrile (0.257 g, 0.87 mmol), prepared in the previous step, was added and the mixture was heated to 170° C. for 2 h then cooled and diluted with ethyl acetate. The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (15% acetone in hexane) afforded the title compound (9 mg, 4%). HRMS: calcd for C15H13N3O3+H+, 284.10297; found (ESI, [M+H]+), 284.1024; Analytical HPLC: purity 95.3% at 210-370 nm, 8.1 min; 98.3% at 278 nm, 8.1 min; the Xterra® RP18 column, 3.5%, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

additionwas added
additionwas added
temperaturethen cooled
washwashed with water, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a307bf76de29461ea1606f89ac254fe7
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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