Triphosgene → 6-(3-Chloro-phenyl)4-phenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 413119Notes

Reaction equation

HRID 413119 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]=1C1(C=CC=CC1)CO.Cl[C:24](Cl)([O:26][C:27](=[O:33])OC(Cl)(Cl)Cl)Cl>>[Cl:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:27](=[O:33])[O:26][CH:24]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:3]=3[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 94429TriphosgeneHCID 689437431-(4-Amino-3'-chloro-biphenyl-3-yl)-benzyl alcohol

Product 1

HCID 98191116-(3-Chloro-phenyl)4-phenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Procedure

Prepared from 1-(4-amino-3′-chloro-biphenyl-3-yl)-benzyl alcohol and triphosgene according to the procedure of Example 9. Off-white solid: mp 177-178° C.; 1H-NMR (DMSO-d6) δ10.5 (s, 1H), 7.68 (dd, 1H, J=8.7, 1.7 Hz), 7.62 (t, 1H, J=1.74 Hz), 7.54-7.5 (m, 1H), 7.48-7.34 (m, 8H), 7.04 (d, 1H, J=8.7 Hz), 6.6 (s,1H); MS (ESI) m/z 336 ([M+H]+, 30%).

Sources & evidence

ORD record
ord-c65fb763edd347078b43308efe198ac9
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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