Tetrahydrofuran → HCID 10154853, compound

HRID 1793374Notes

Reaction equation

HRID 1793374 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]1([Mg]Br)C=[CH:22][CH:21]=[CH:20][CH:19]=1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1.[CH2:38]1COCC1>>[Cl:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:31](=[O:32])[O:17][C:15]([CH3:38])([C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:3]=3[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 159081311-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 10154853HCID 10154853, compound

Procedure

6-(3-Chlorophenyl)-4-methyl-4-phenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, from 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (0.2 g, 0.82 mmol) and phenylmagnesium bromide followed by treatment with CDI in THF, as a white solid: mp 179–180° C.; 1H-NMR (CDCl3) δ 8.27 (s, 1H, D2O exchangeable), 7.51–7.57 (m, 2H), 7.28–7.45 (m, 9H), 6.92 (d, 1H, J=8.4 Hz), 2.12 (s, 3H); MS (ESI) m/z 348 ([M−H]−, 100%); Anal. Calc. For C21H16ClNO2: C, 72.10, H, 4.61, N, 4.00. Found: C, 71.72, H, 4.86, N, 3.91.

Sources & evidence

ORD record
ord-32cecf2ca50b4412a37e97546a0bac8c
Source dataset
uspto-grants-2006_07
Patent number
US07081457B2

Reaction notes

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