Chloroacetone → HCID 10401849, compound

HRID 1650656Notes

Reaction equation

HRID 1650656 reaction equation
[CH2:1]([C:3]1[C:4]([O:16][CH3:17])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13](=[S:15])[NH2:14])[N:12]=2)[C:8]=1[CH3:9])[CH3:2].Cl[CH2:19][C:20](=O)[CH3:21]>C(O)C>[CH2:1]([C:3]1[C:4]([O:16][CH3:17])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]3[S:15][CH:19]=[C:20]([CH3:21])[N:14]=3)[N:12]=2)[C:8]=1[CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 6571Chloroacetone2×HCID 14234968HCID 14234968, compound

Product 1

HCID 10401849HCID 10401849, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.30 g (0.017 mol) of 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-thiocarboxamide and 3.18 g (0.0344 mol; 2 eq) of chloroacetone in 300 ml of ethanol was heated under reflux. After 5 hours, 3.18 g of more chloroacetone were added. After 29 hours, the solvent was evaporated, and the residue was dissolved in 2000 ml of water. The solution was made alkaline with concentrated ammonia and was extracted 3 times with chloroform. The chloroform extracts were dried over MgSO4, filtered and evaporated to dryness. The residue was purified by flash chromatography using chloroform as eluent and the resulting solid was recrystallized from ethyl acetate to obtain 3.37 g (68%) of 6-ethyl-7-methoxy-5-methyl-2-(4-methylthiazol-2-yl)-imidazo[1,2-a]pyrimidine as a buff powder melting at 184°-186° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. waitAfter 29 hours
  4. customthe solvent was evaporated
  5. dissolutionthe residue was dissolved in 2000 ml of water
  6. extractionwas extracted 3 times with chloroform
  7. dry with materialThe chloroform extracts were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by flash chromatography
  11. customthe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2bb60d4eb3a04ea7b4e7490879f9eb57
Source dataset
uspto-grants-1990_05
Patent number
US04925846

Reaction notes

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