Cyanuric chloride → 2,4-Dichloro-6-morpholino-1,3,5-triazine

HRID 2395621Notes

Reaction equation

[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>COCCOC>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:7]=1

Participants

Conditions

Temperature: -15 °C

Procedure

Cyanuric chloride (7.30 g, 39.6 mmol) was dissolved in ethylene glycol dimethyl ether (100 ml), cooled to -15° C. and gradually added dropwise with morpholine (7.00 ml, 80.3 mmol) dissolved in ethylene glycol dimethyl ether (50 ml). This reaction mixture was stirred at the same temperature for 30 minutes and then stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure. The residue was added with dichloromethane and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography, using n-hexane and ethyl acetate (6:4) as eluant, to obtain 6.32 g (yield: 68.0%) of 2,4-dichloro-6-morpholino-1,3,5-triazine as colorless crystals having melting point of 160.5° C.-161° C.

Workup

stirringstirred at room temperature overnight
customThe reaction mixture was evaporated under reduced pressure
additionThe residue was added with dichloromethane and water
stirringshaken
additionfor mixing
customThe organic layer was separated from the mixture
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-24547553f6a648f1b4242ebad1b7d6c9
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489591

Reaction notes

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