1,1'-Carbonyldiimidazole → 6-(3-Chlorophenyl)-4-ethynyl-4-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1725030Notes

Reaction equation

HRID 1725030 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[C:18]([Mg]Br)#[CH:19].C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1>>[Cl:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:27](=[O:28])[O:17][C:15]([C:18]#[CH:19])([CH3:16])[C:3]=3[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 159081311-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanoneHCID 178418486HCID 178418486, compound

Product 1

HCID 98792996-(3-Chlorophenyl)-4-ethynyl-4-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Procedure

Prepared from 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (0.2 g, 0.82 mmol) and ethynylmagnesium bromide followed by treatment with CDI according to procedure C. Off-white solid: mp 185-186° C.; 1H-NMR (CDCl3) δ 8.18 (s, 1H, D2O exchangeable), 7.53 (t, 1H, J=1.7 Hz), 7.49 (s, 1H), 7.31-7.48 (m, 4H), 6.92 (d, 1H, J=8.1 Hz), 2.81 (s, 1H), 1.87 (s, 3H); MS (ESI)m/z 304 ([M−H]−, 100%); Anal. Calc. For C17H12ClNO2: C, 68.58; H, 4.06; N, 4.70. Found: C, 68.24; H, 3.94; N, 4.65.

Sources & evidence

ORD record
ord-75410deaad4948d38e77300d8db15be3
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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