Phosgene → HCID 44137272, compound

HRID 2045829Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:23])([CH2:20][CH:21]=[CH2:22])[CH2:9][CH2:10][NH:11][N:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:24](Cl)(Cl)=[O:25]>C(N(CC)CC)C.C1(C)C=CC=CC=1.C(Cl)(Cl)=O>[CH2:20]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:23][C:24](=[O:25])[N:11]([N:12]([CH3:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:10][CH2:9]1)[CH:21]=[CH2:22]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-fluorophenyl)-1-(2-methyl-2-phenylhydrazinyl)hex-5-en-3-ol (14 mg, 0.04 mmol) and triethylamine (3 drops) was dissolved in toluene (1 mL). The solution was cooled to 0° C. and phosgene (3 drops, 20% toluene solution) was added. After 1 h, more phosgene was added (3 drops, 20% toluene solution) and the reaction was allowed to warm to rt overnight. The solvent was evaporated and the residue was redissolved in toluene. DBU (5 drops) was added and the solution heated to reflux for 4 h. The solvent was evaporated and the residue was purified by preparative HPLC to afford 6-allyl-6-(4-fluorophenyl)-3-(methyl(phenyl)amino)-1,3-oxazinan-2-one (8.8 mg). LC-MS Method 1 m/z=341 (M+1). 1H NMR (CDCl3) δ 7.43-7.37 (br m), 7.25-7.26 (m), 7.19-7.12 (m), 6.99 (t), 6.85 (m), 6.72-6.66 (m), 6.07 (d), 6.73 (m), 5.15-5.05 (m), 3.42 (m), 3.33 (m), 3.14 (s), 2.85 (s), 2.65-2.55 (m), 2.50-2.34 (m).

Workup

temperatureto warm to rt overnight
customThe solvent was evaporated
dissolutionthe residue was redissolved in toluene
additionDBU (5 drops) was added
temperaturethe solution heated
temperatureto reflux for 4 h
customThe solvent was evaporated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-71e2b73ef4554e86877dc9cff5e7361d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592409B2

Reaction notes

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