Brofoxine → 6-Bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-thione

HRID 2400389Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=O)[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[S:24])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 30630Brofoxine

HCID 87949Lawesson's reagent

Product 1

HCID 98383546-Bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-thione

Procedure

The product was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and Lawesson's reagent using the procedure of Example 9, as a white solid: mp 221-222.5° C.; 1H-NMR (CDCl3) δ 9.38 (s, 1H, D2O exchangeable), 7.42 (dd, 1H, J=8.5, 2.1 Hz), 7.29 (d, 1H, J=2.0 Hz), 6.76 (d, 1H, J=8.4 Hz), 1.76 (s, 6H); MS (EI) m/z 272 ([M+H]+, 94%), 274 ([M+H]+, 100%).

Sources & evidence

ORD record: ord-0cdbb117263c4b3380ec13dd6783c8e4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796266B2

Reaction notes

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