Brofoxine → 6-(2-Chlorophenyl)-4,4-dimethyl-1H-benzo[D][1,3]oxazin-2(4H)-one

HRID 2304523Notes

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:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[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

Participants

Reactant 2

HCID 30630Brofoxine

HCID 27343222-Chlorophenylboronic acid

Product 1

HCID 98607216-(2-Chlorophenyl)-4,4-dimethyl-1H-benzo[D][1,3]oxazin-2(4H)-one

Procedure

6-(2-Chloro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, according to the procedure of Example 4 from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 2-chlorophenyl boronic acid, as a white solid: mp 181-182 ° C.; MS (ESI) m/z 288 ([M+H]+, 70%), Anal. Calc. For C16H14ClNO2: C, 66.79; H, 4.90; N, 4.87; Found: C, 66.78; H, 4.82; N, 4.55.

Sources & evidence

ORD record: ord-6e32d3398b9f465e921926cc6ebed30d
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436929B1

Reaction notes

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