Triphosgene → 4-Benzyl-6-(3-chlorophenyl)-4-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 413139Notes

Reaction equation

HRID 413139 reaction equation
[CH2:1]([C:4]1([CH3:22])[O:9][C:8](=[O:10])[NH:7][C:6]2[CH:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)=[CH:14][C:5]1=2)[CH:2]=[CH2:3].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH2:1]([C:4]1([CH3:22])[O:9][C:8](=[O:10])[NH:7][C:6]2[CH:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)=[CH:14][C:5]1=2)[C:2]1[CH:3]=[CH:2][CH:1]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 9836471HCID 9836471, compound

Product 1

HCID 102701074-Benzyl-6-(3-chlorophenyl)-4-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-oneYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-amino-3′-chloro-biphenyl-3-yl)-1-benzyl-ethanol (prepared using 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone and benzylmagnesium bromide according to Procedure C, 0.14 g, 0.42 mmol) and triphosgene (0.04 g, 0.14 mmol) in dry THF (10 mL) was stirred under a blanket of nitrogen for 10 minutes. Upon completion of the reaction, the THF was removed and the residue purified via flash chromatography (silica gel, 35% ethyl acetate/hexane) to give 4-benzyl-6-(3-chloro-phenyl)-4-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (0.045 g, 30%) as an off-white solid: mp 187-188° C.; 1H-NMR (DMSO-d6) δ10.1 (s, 1H), 7.70 (t, 1H, J=2.3 Hz), 7.6 (d, 1H, J=8.0 Hz), 7.58-7.53 (m, 2H), 7.46 (t, 1H, J=8.0 Hz), 7.38 (d, 1H, J=8.0 Hz), 7.22-7.17 (m, 3H), 7.06-7.0 (m, 2H), 6.84 (d, 1H, J=9.14 Hz), 3.24 (d, 1H, J=14.3 Hz), 3.06 (d, 1H, J=14.3 Hz), 1.68 (s, 3H); MS (ESI) m/z 364 ([M+H]+, 100%); Anal. Calc. For C22H18ClNO2: C,72.63; H, 4.99; N, 3.85. Found: C, 71.82; H,5.09; N,3.58.

Workup

  1. customUpon completion of the reaction
  2. customthe THF was removed
  3. customthe residue purified via flash chromatography (silica gel, 35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9f1b16bf92b449e588ab7a85a74a62ab
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

Loading…