2-Bromobenzyl cyanide → 2-(4,4-Dimethyl2-oxo-1,4-dihydro-2H-benzo[d][1,3]-oxazin-6-yl)phenylacetonitrile

HRID 1725082Notes

Reaction equation

HRID 1725082 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[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>>[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:7]=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:8][C:9]#[N:10])=[CH:18][C:17]1=2

Participants

3

Reactant 2

HCID 296252-Bromobenzyl cyanideHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 235096112-(4,4-Dimethyl2-oxo-1,4-dihydro-2H-benzo[d][1,3]-oxazin-6-yl)phenylacetonitrile

Procedure

Prepared according to procedure B from 2-bromophenylacetonitrile and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid. White solid; mp 176-179° C.; 1H-NMR (DMSO-d6), δ 10.31 (s, 1H), 7.53 (m, 1H), 7.48 (m,2H), 7.22-7.32 (m,3H), 6.98 (d,1H; J=8.0 Hz), 3.90 (s,2H), 1.64 (s,6H). MS (+)APCI [M+H]+ m/z=293. Anal. Calc. For C18H16N2O2: C, 73.95; H, 5.52; N, 9.58. Found: C, 73.51; H, 5.70; N, 9.39.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a33842af00ea437cbc0bddbefb52a156
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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