Acetyl chloride → Acetamide, N-(4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-

HRID 1031867Notes

Reaction equation

HRID 1031867 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:9]=[C:8]([CH2:18][CH2:19][CH3:20])[N:7]=1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[O:15]1[CH2:14][CH2:13][N:12]([C:10]2[N:9]=[C:8]([CH2:18][CH2:19][CH3:20])[N:7]=[C:6]([NH:5][C:1](=[O:3])[CH3:2])[N:11]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 3080166HCID 3080166, compound

Product 1

HCID 3080135Acetamide, N-(4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-Yield 43.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

4 g (0.05 mole) of acetyl chloride are added dropwise into a solution of 11.2 g (0.05 mole) of 2-amino-4-morpholino-6-propyl-1,3,5-triazine in 100 ml of anhydrous pyridine at room temperature. The mixture is stirred for 6 hours and then allowed to stand for 48 hours. The pyridine hydrochloride is filtered off and the filtrate is evaporated under reduced pressure. The residue obtained is taken up once in toluene, and the mixture is evaporated again. The residue is then taken up in dichloromethane and the solution is washed with water and dried over sodium sulfate. The residue obtained after evaporation of the solvent is purified by chromatography over silica (eluent: 90:10 v/v) dichloromethane-ethanol) and the product is finally recrystallized from ethyl acetate. 5.75 g of N-(4-morpholino-6-propyl-1,3,5-triazin-2-yl)-acetamide are obtained. Yield: 43.4%. M.P.: 141°-142° C. (Compound 21a). Hydrochloride: M.P.: 145°-146° C. (isopropyl alcohol-ether). (Compound 21b).

Workup

  1. waitto stand for 48 hours
  2. filtrationThe pyridine hydrochloride is filtered off
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue obtained
  5. customthe mixture is evaporated again
  6. washthe solution is washed with water
  7. dry with materialdried over sodium sulfate
  8. customThe residue obtained
  9. customafter evaporation of the solvent
  10. customis purified by chromatography over silica (eluent: 90:10 v/v) dichloromethane-ethanol) and the product
  11. customis finally recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ed5833f930894e0e900a8a8b68f130fe
Source dataset
uspto-grants-1990_09
Patent number
US04956363

Reaction notes

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