Morpholine → 2-Chloro-4-cyclopropyl-6-morpholino-1,3,5-triazine

HRID 256709Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:13]=[C:12](Cl)[N:11]=[C:10]([CH:15]2[CH2:17][CH2:16]2)[N:9]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[Cl:7][C:8]1[N:9]=[C:10]([CH:15]2[CH2:17][CH2:16]2)[N:11]=[C:12]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:13]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 2.61 g (0.03 mole) of morpholine in 20 ml of chloroform is added in the course of 30 minutes to a solution of 5.7 g (0.03 mole) of 2,4-dichloro-6-cyclopropyl-1,3,5-triazine in 50 ml of chloroform, cooled to between 3° and 5° C. The temperature of the mixture is allowed to return to about 10° C., then the mixture is cooled again to 5° C. and a solution of 4.14 g (0.03 mole) of potassium carbonate in 15 ml of water is added dropwise. The mixture is then stirred at room temperature for two hours. 30 ml of water are added and the organic phase is separated off. The solution is washed with water and dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica (eluent: 96.5:3.5 (v/v) dichloromethane-ethylacetate) and then recrystallized from hexane. 5.5 g of 2-chloro-4-cyclopropyl-6-morpholino-1,3,5-triazine are thus obtained. Yield: 76.2%. M.P.: 99°-100° C.

Workup

temperaturecooled to between 3° and 5° C
customto return to about 10° C.
customthe organic phase is separated off
washThe solution is washed with water
dry with materialdried over sodium sulfate
customthe solvent is evaporated under reduced pressure
customThe residue is purified by chromatography on silica (eluent: 96.5:3.5 (v/v) dichloromethane-ethylacetate)
customrecrystallized from hexane

Sources & evidence

ORD record: ord-3cfee7b7e7a1454599bd237dd79c0e39
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258513

Reaction notes

Loading…