Methyl iodide → 7-amino-8-[(4-chlorophenyl)methyl]-2-methyl-6-nitroso-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one

HRID 236018Notes

Reaction equation

HRID 236018 reaction equation
[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=S)[NH:3]1.CI.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.[Na].[N:20](=[C:22]([C:28]#[N:29])[C:23](OCC)=[O:24])[OH:21]>CCO>[NH2:29][C:28]1[N:16]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:4]2[N:5]([CH2:6][CH:2]([CH3:1])[N:3]=2)[C:23](=[O:24])[C:22]=1[N:20]=[O:21]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 660364-ChlorobenzylamineHCID 27773124-Methylimidazolidine-2-thioneHCID 5360545SodiumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 1784298247-amino-8-[(4-chlorophenyl)methyl]-2-methyl-6-nitroso-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred suspension of 4-methylimidazoline-2-thione (45.0 g., 0.387 mole; purified by water recrystallization) in ethanol (200 ml., dried over 4A molecular sieve), methyl iodide (54.9 g., 0.387 mole) was added dropwise. The reaction was stirred at room temperature for 4 hr. during which time the solid dissolved. To this solution 4-chlorobenzylamine (54.8 g., 0.387 mole) was added and the solution was heated at reflux for 16 hrs. This solution was added while hot to a solution of sodium (35.6 g., 1.55 gram atom) in ethanol (900 ml., dried over 4A molecular sieve), and ethyl oximinocyanoacetate (5.50 g., 0.387 mole) was added in portions. The mixture was refluxed for 3 hrs. and concentrated in vacuo. Water (600 ml.) was added to the residue and the solution neutralized with HOAc. The orange precipitate was collected, washed with CH3CN and Et2O to give 95.6 g. (77%) orange solid, m.p. 222° -223° (dec.).

Workup

  1. additionwas added dropwise
  2. dissolutionduring which time the solid dissolved
  3. temperaturethe solution was heated
  4. temperatureat reflux for 16 hrs
  5. additionwas added in portions
  6. temperatureThe mixture was refluxed for 3 hrs
  7. concentrationand concentrated in vacuo
  8. additionWater (600 ml.) was added to the residue
  9. customThe orange precipitate was collected
  10. washwashed with CH3CN and Et2O
  11. customto give 95.6 g

Sources & evidence

ORD record
ord-1eb7f690b6f448faa500c11c57459383
Source dataset
uspto-grants-1987_02
Patent number
US04642345

Reaction notes

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