Acetone → 2-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazine

HRID 2037051Notes

Reaction equation

HRID 2037051 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CC(C)=[O:25]>O>[Cl:3][C:2]1[N:1]=[C:8]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:7]=[C:5]([N:12]2[CH2:13][CH2:14][O:25][CH2:16][CH2:15]2)[N:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7954Cyanuric chlorideHCID 8083MorpholineHCID 8471Triethylamine

Product 1

HCID 2249672-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of cyanuric chloride (18.4 g, 10 mmol) in acetone (100 ml) and crushed ice (500 g), a mixture of triethylamine (30.0 g, excess) and morpholine (17.4 g, 20 mmol) was added at −10° C. After the addition, reaction mixture was stirred at room temperature and for 1 hour and diluted with 50 ml water. Separated white solid was filtered and washed with water. The white solid was dried and filtered. The crude product was found to be pure and taken to next step without purification. Yield: 25 g, 87%; (M+H) 286.7

Workup

  1. additionwas added at −10° C
  2. additionAfter the addition, reaction mixture
  3. customSeparated white solid
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe white solid was dried
  7. filtrationfiltered
  8. customtaken to next step without purification

Sources & evidence

ORD record
ord-3c79ad92d4df4d588bd5144769af2e3b
Source dataset
uspto-grants-2013_11
Patent number
US08575159B2

Reaction notes

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