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

HRID 256709
Notes
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Reaction equation

HRID 256709 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 189652202,4-Dichloro-6-cyclopropyl-1,3,5-triazine

Product 1

HCID 189652072-Chloro-4-cyclopropyl-6-morpholino-1,3,5-triazineYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 6212
Chloroform
Solvent
2×

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

  1. temperaturecooled to between 3° and 5° C
  2. customto return to about 10° C.
  3. customthe organic phase is separated off
  4. washThe solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is purified by chromatography on silica (eluent: 96.5:3.5 (v/v) dichloromethane-ethylacetate)
  8. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes