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

HRID 1635003Notes

Reaction equation

HRID 1635003 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([CH3:26])[C:17]2[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:16]=2[NH:15][C:14](=[O:25])[O:13]1>O>[CH3:11][C:12]1([CH3:26])[O:13][C:14](=[O:25])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:2]3[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=3)=[CH:18][C:17]1=2

Participants

4

Reactant 2

HCID 36023(3-Bromophenyl)acetonitrileHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

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 according to the procedure B from 3-bromophenylacetonitrile and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-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)2. 0.3 H2O: C,72.61, H, 5.62, N, 9.41. Found: C, 73.00, H,5.43, N, 8.81

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-287efba8f935457fafb32264d4a93833
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

Loading…