(3-Bromophenyl)acetonitrile → 3-(4,4Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]-oxazin-6-yl)phenylacetonitrile

HRID 1882840Notes

Reaction equation

HRID 1882840 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]1([CH3:22])[CH:17]=[C:16](B(O)O)[NH:15][C:14](=[O:21])[O:13]1>O>[CH3:11][C:12]1([CH3:22])[O:13][C:14](=[O:21])[NH:15][C:16]2[CH:3]=[CH:2][C:7]([C:2]3[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=3)=[CH:6][C:17]1=2

Participants

4

Reactant 2

HCID 36023(3-Bromophenyl)acetonitrileHCID 23509607HCID 23509607, compound

Product 1

HCID 120945053-(4,4Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]-oxazin-6-yl)phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared from 3-bromophenylacetonitrile and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-oxazin-6-yl)boronic acid. White solid: mp 188-190° C.; 1H-NMR (DMSO-d6) δ10.33 (s, 1H), 7.62 (m, 2H), 7.55 (m, 2H), 7.48 (d, 1H, J=8.00 Hz), 7.33 (d, 1H, J=7.57 Hz), 6.99 (d, 1H, J=8.81 Hz), 4.09 (s, 2H), 1.67 (s, 6H); MS m/z 291(M−H). Anal. Calc. For C18H16N2O2.0.3 H2O: C, 72.61; H, 5.62; N, 9.41. Found: C, 73.00; H, 5.43; N, 8.81

Sources & evidence

ORD record
ord-26fc6a36a5a743d89c01391279fe90dd
Source dataset
uspto-grants-2004_07
Patent number
US06759408B2

Reaction notes

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