Potassium Carbonate → 6-(3-Ethynyl-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 50720Notes

Reaction equation

HRID 50720 reaction equation
[CH3:1][C:2]1([CH3:25])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][Si](C)(C)C)[CH:14]=3)=[CH:12][C:3]1=2.C(=O)([O-])[O-].[K+].[K+]>CO>[C:19]([C:15]1[CH:14]=[C:13]([C:11]2[CH:10]=[CH:9][C:4]3[NH:5][C:6](=[O:8])[O:7][C:2]([CH3:25])([CH3:1])[C:3]=3[CH:12]=2)[CH:18]=[CH:17][CH:16]=1)#[CH:20]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 99029764,4-Dimethyl-6-(3-trimethylsilanylethynyl-phenyl)-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 98141916-(3-Ethynyl-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4,4-dimethyl-6-(3-trimethylsilanylethynyl-phenyl)-1,4-dihydro-benzo[d][1,3]oxazin-2-one (0.7 g, 2 mmol) and potassium carbonate (2 g, excess) in anhydrous methanol was stirred at rt under nitrogen for 4 hours. The mixture was treated with ice-water (100 mL) and extracted with ethyl acetate (2×80 mL). The organic layers were washed with brine and dried with MgSO4. The solvent was removed and the title compound was obtained as a off-white solid (0.4 g, 72%): mp 171-172° C. 1H-NMR (DMSO-d6) δ 10.3, (s, 1H), 7.78 (bs, 1H), 7.72-7.69 (m, 1H), 7.6-7.57 (m, 2H), 7.49-7.43 (m, 2H), 6.97 (d, 1H, J=7.98 Hz), 4.25 (s, 1H), 1.67 (s, 6H); MS (EI) m/z 277([M+], 100%), Anal. Calc. For C18H15NO2.0.2 EtOAc: C, 76.56; H, 5.67; N, 4.75. Found: C, 76.34; H, 5.4; N, 4.7.

Workup

  1. extractionextracted with ethyl acetate (2×80 mL)
  2. washThe organic layers were washed with brine
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-c3b61bbd7b674cdd94e0aecd7f88ffc1
Source dataset
uspto-grants-2004_03
Patent number
US06713478B2

Reaction notes

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