Hydrochloric Acid → 4-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbaldehyde

HRID 1882863Notes

Reaction equation

HRID 1882863 reaction equation
C([O:3][CH:4](OCC)[C:5]1[O:9][CH:8]=[C:7]([C:10]2[CH:22]=[CH:21][C:13]3[NH:14][C:15](=[O:20])[O:16][C:17]([CH3:19])([CH3:18])[C:12]=3[CH:11]=2)[CH:6]=1)C.Cl>C1COCC1>[CH3:18][C:17]1([CH3:19])[O:16][C:15](=[O:20])[NH:14][C:13]2[CH:21]=[CH:22][C:10]([C:7]3[CH:6]=[C:5]([CH:4]=[O:3])[O:9][CH:8]=3)=[CH:11][C:12]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 235096166-(5-Diethoxymethyl-furan-3-yl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 235096234-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-(5-diethoxymethyl-furan-3-yl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1.1 g, 3 mmol) was stirred in THF (20 mL) and 2N HCl (2 mL) for 1 hour. The crystalline product was filtered and dried (0.52 g, 69%): mp 262-263° C.; 1H NMR (DMSO-d6) δ10.3 (s, 1H), 9.65 (s, 1H), 8.59 (s, 1H), 8.04 (s, 1H), 7.65-7.64 (d, 1H, J=1.5 Hz), 7.61-7.60 (d, 1H, J=1.8 Hz), 7.59-7.58 (d, 1H, J=1.8 Hz), 6.94-6.91 (d, 1H, J=8.2 Hz), 1.65 (s, 6H). MS (ESI) m/z 270 [M−H]−.

Workup

  1. filtrationThe crystalline product was filtered
  2. customdried (0.52 g, 69%)

Sources & evidence

ORD record
ord-3b0580cb75dd4e939411d9b048a2f9ca
Source dataset
uspto-grants-2004_07
Patent number
US06759408B2

Reaction notes

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