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

HRID 1665450Notes

Reaction equation

HRID 1665450 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-ae363006675b454ea62be370370f3077
Source dataset
uspto-grants-2011_10
Patent number
US08039469B2

Reaction notes

Loading…