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

HRID 413118Notes

Reaction equation

HRID 413118 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[CH:15]([OH:18])[CH2:16][CH3:17].Cl[C:20](Cl)([O:22]C(=O)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:20](=[O:22])[O:18][CH:15]([CH2:16][CH3:17])[C:3]=3[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 94429TriphosgeneHCID 23509612HCID 23509612, compound

Product 1

HCID 98388746-(3-Chloro-phenyl)4-ethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Procedure

Prepared according to the procedure of Example 9 from 1-(4-amino-3′-chloro-biphenyl-3-yl)-propanol and triphosgene. White solid: mp 146-148° C.; 1H-NMR (DMSO-d6) δ10.3 (s, 1H), 7.70 (m, 1H), 7.60 (m, 3H), 7.47 (t, 1H, J=8.22 Hz), 7.39 (d, 1H, J=8.28 Hz), 6.97 (d, 1H, J=8.22 Hz), 5.4 (t, 1H, J=10.9 Hz), 1.9 (m, 2H), 0.97 (t, 3H, J=7.68 Hz); MS (ESI) m/z 286 ([M−H]−, 100%)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-138c06f7b956463da217f4d2929137e6
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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