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

HRID 1634953Notes

Reaction equation

HRID 1634953 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:17])[CH3:16])(Cl)[CH2:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[Cl:25]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C1[CH2:41][O:40]CC1>>[CH2:18]([C:15]1([CH3:16])[O:17][C:41](=[O:40])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([Cl:25])[CH:9]=3)=[CH:4][C:3]1=2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 94429TriphosgeneHCID 22736630HCID 22736630, compound

Product 1

HCID 102701074-Benzyl-6-(3-chlorophenyl)-4-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-oneYield 30%

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-chlorophenyl)-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-00e1d8137ffd467d9b52cf4d60324172
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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