Brofoxine → 6-(3,5Dichloro-phenyl)4,4-dimethyl-1,4-dihydrobenzo[d][1,3]-oxazin-2-one

HRID 1258091Notes

Reaction equation

HRID 1258091 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[O:12])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([Cl:22])[CH:21]=1>>[Cl:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:14]=[CH:13][C:5]3[NH:6][C:7](=[O:12])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=3[CH:3]=2)[CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

3

Reactant 2

HCID 30630BrofoxineHCID 27343313,5-Dichlorophenylboronic acid

Product 1

HCID 99271486-(3,5Dichloro-phenyl)4,4-dimethyl-1,4-dihydrobenzo[d][1,3]-oxazin-2-one

Procedure

6-(3,5-dichloro-phenyl)-4,4-dimethyl-1,4-dihydrobenzo-[d][1,3]oxazin-2-one was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 3,5-dichlorophenyl boronic acid according to the procedure of Example 4, as a white solid: mp 245-246° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 7.77 (m, 2H), 7.67-7.64 (m, 2H), 7.56 (bs, 1H), 6.96 (d, 1H, J=7.98 Hz), 1.7 (s, 6H); MS (EI) m/z 321 ([M+H]+, 40%); Anal. Calcd. For C16H13Cl2NO2: C, 59.32; H, 4.11; N, 4.32. Found: C, 59.13; H, 4.29; N, 4.17.

Sources & evidence

ORD record
ord-8fc9dc26eec44a608fa9dba77cc457b8
Source dataset
uspto-grants-2013_06
Patent number
US08466146B2

Reaction notes

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