Toluene → 3-(3-Fluoro-4-isopropyl-phenyl)-5-methyltetrahydro-1,3,5-oxadiazin-4-one

HRID 262931

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([NH:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9].CN(C)[CH:18]=[O:19].[C:21]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:11]2[C:12](=[O:13])[N:14]([CH3:21])[CH2:15][O:19][CH2:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

N-(3-Fluoro-4-isopropyl-phenyl)-N'-methyl-urea (one mol=210 g.) and polyoxymethylene (1 mol=90 g.) are dissolved in toluene (800 cc.) in the presence of para-toluenesulphonic acid (0.3 mol=51.6 g.) as a catalyst and of dimethylformamide (0.3 mol=22 g.), and the mixture is heated for 15 minutes at 80° C. After having washed the solution with water and then concentrated it, 3-(3-fluoro-4-isopropyl-phenyl)-5-methyltetrahydro-1,3,5-oxadiazin-4-one is obtained in the form of an oil which is purified by dissolving in hot hexane and recrystallising.

Workup

washAfter having washed the solution with water
concentrationconcentrated it

Sources & evidence

ORD record: ord-510a4bf1a90642f583f7a61a6c0b2b29
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04155747

Linked notes

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