Ethyl Acetate → (6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide

HRID 1295945Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]#[N:10].[C:11]([C:15]1[C:24]2[O:23][CH2:22][CH2:21][NH:20][C:19]=2[CH:18]=[C:17]([C:25](=[O:27])[CH3:26])[CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(OCC)(=O)C>CN(C)C=O>[C:25]([C:17]1[CH:16]=[C:15]([C:11]([CH3:14])([CH3:12])[CH3:13])[C:24]2[O:23][CH2:22][CH2:21][N:20]([CH2:8][C:9]#[N:10])[C:19]=2[CH:18]=1)(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 90 °C

Procedure

Potassium carbonate (3.6 g, 26 mmol) and bromoacetonitrile (15.4 g, 128.6 mmol) were added to a solution of 1-[8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone (6.0 g, 25.5 mmol) in dimethylformamide (100 ml) and the mixture was stirred at 90° C. for 6 hours. Ethyl acetate was added, the reaction mixture was washed with water and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (6.9 g) as a light yellow oil.

Workup

washthe reaction mixture was washed with water and brine in that order
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record: ord-8d087dac437c456c90fa4b3cda795f08
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244730B2

Reaction notes

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