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

HRID 1408457Notes

Reaction equation

HRID 1408457 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.O>C(Cl)Cl>[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

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8083Morpholine

Product 1

HCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanuric chloride (10.0 g, 54.2 mmol, 1.0 eq.) was dissolved in methylene chloride (60 ml) and morpholine (4.70 ml, 54.2 mmol, 1.0 eq.) was slowly added (drop by drop) to the reaction mixture at −50° C., stirred for 20 minutes at the same temperature and poured into water. After extraction with methylene chloride and ethyl acetate (2×), the organic layers were dried over MgSO4 and concentrated. Further purification was done by flash chromatography (1:1 hexane/ethyl acetate) to yield the title compound as a colorless solid (3.56 g, 28%).

Workup

  1. extractionAfter extraction with methylene chloride and ethyl acetate (2×)
  2. dry with materialthe organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. customFurther purification

Sources & evidence

ORD record
ord-e17ae102c7674cc9bb7b1d798cd678bc
Source dataset
uspto-grants-2014_12
Patent number
US08921361B2

Reaction notes

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