Chloroacetyl chloride → 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

HRID 1825754Notes

Reaction equation

Cl[CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:8]=1[OH:15].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:13]([C:11]1[CH:10]=[CH:9][C:8]2[O:15][CH2:2][C:3](=[O:4])[NH:6][C:7]=2[CH:12]=1)#[N:14]

Participants

Conditions

Temperature: 0 °C

Procedure

Chloroacetyl chloride (3.12 ml, 38 mmol) was added dropwise to a solution of 2-amino-4-cyanophenol (4.96 g, 37 mmol), triethylamine (10.98 ml, 78 mmol) and 4-(dimethylamino)pyridine (0.09 g, 0.74 mmol) in dry dichloromethane (40 ml) maintained at 0° C. The solution refluxed for 24 h. The reaction mixture was cooled, and the organic layer was washed with phosphoric acid (0.5 M), saturated sodium bicarbonate, water and brine, then dried with anhydrous magnesium sulfate. The organic layer was filtered, then evaporated to dryness. The residue was recrystalized from ethanol to afford 3.9 g (60%) of the titled compound. (mp 243–245° C.).

Workup

temperatureThe solution refluxed for 24 h
temperatureThe reaction mixture was cooled
washthe organic layer was washed with phosphoric acid (0.5 M), saturated sodium bicarbonate, water and brine
dry with materialdried with anhydrous magnesium sulfate
filtrationThe organic layer was filtered
customevaporated to dryness
customThe residue was recrystalized from ethanol

Sources & evidence

ORD record: ord-ab3610c8b0b94044b4032d83649745b4
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049312B1

Reaction notes

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