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

HRID 536806Notes

Reaction equation

HRID 536806 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.CCN(CC)CC>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 7954Cyanuric chlorideHCID 8083MorpholineHCID 8471Triethylamine

Product 1

HCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of cyanuric chloride (2.5 g, 13.5 mmol) in CH2Cl2 (150 mL) was added dropwise morpholine (1.14 g, 13.5 mmol) at −78° C., followed by addition of Et3N (3.0 mL, 21.5 mmol). The resulting reaction mixture was stirred at −78° C. for 20 min, and then diluted with CH2Cl2. The organic phase was washed with water and brine, and dried over MgSO4. The solvent was removed in vacuum to give the title compound as white crystalline solid (3.027 g, 95% yield). MS (ESI) m/z 235.1.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-7ce22fefe1ab409e8687b98257c37682
Source dataset
uspto-grants-2014_10
Patent number
US08859542B2

Reaction notes

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