(3-Chlorophenyl)boronic acid → 6-(3-Chlorophenyl)4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

HRID 2400422Notes

Reaction equation

HRID 2400422 reaction equation
[CH2:1]([C:3]1([CH2:15][CH3:16])[O:8][C:7](=[O:9])[NH:6][C:5]2[CH:10]=[CH:11][C:12](I)=[CH:13][C:4]1=2)[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>>[Cl:17][C:18]1[CH:23]=[C:22]([C:12]2[CH:11]=[CH:10][C:5]3[NH:6][C:7](=[O:9])[O:8][C:3]([CH2:15][CH3:16])([CH2:1][CH3:2])[C:4]=3[CH:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 220218924,4-Diethyl-1,4-dihydro-6-iodo-2H-3,1-benzoxazin-2-one

Product 1

HCID 102678156-(3-Chlorophenyl)4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

Procedure

6-(3-Chlorophenyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one was prepared, from 4,4-diethyl-6-iodo-1,4-dihydrobenzo[d][1,3]oxazin-2-one and 3-chlorophenyl boronic acid according to the procedure of Example 4, as a white solid: mp 150-151° C.; 1H-NMR (CDCl3) δ 8.52 (s, 1H, D2O exchangeable), 7.50 (s, 1H), 7.31-7.44 (m, 4H), 7.16 (d, 1H, J=1.5 Hz), 6.89 (d, 1H, J=8.2 Hz), 2.03 (m, 4H), 0.94 (t, 6H, J=7.4 Hz); MS (EI) m/z 315 (M+, 53%). Anal. Calcd. For C18H18ClNO2: C, 68.46; H, 5.75; N, 4.44. Found: C, 68.16; H, 5.81; N, 4.32.

Sources & evidence

ORD record
ord-0b8e3a2edac7444c9ee57dde0b5406c4
Source dataset
uspto-grants-2014_08
Patent number
US08796266B2

Reaction notes

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