Methanol → 1,6-Dihydro-5(4H)-pyrimidinone O-(phenylmethyl)oxime monohydrochloride

HRID 129820

Reaction equation

HRID 129820 reaction equation
O.[ClH:2].Cl.[NH2:4][CH2:5][C:6]([CH2:8][NH2:9])=O.Cl.[C:11]1([CH2:17][O:18][NH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:20]O>>[ClH:2].[C:11]1([CH2:17][O:18][N:19]=[C:6]2[CH2:8][NH:9][CH:20]=[N:4][CH2:5]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 102312Benzyloxyamine hydrochlorideHCID 190837391,3-Diaminopropan-2-one--hydrogen chloride--water (1/2/1)

Product 1

HCID 736056261,6-Dihydro-5(4H)-pyrimidinone O-(phenylmethyl)oxime monohydrochlorideYield 60%

Procedure

1,3-Diaminoacetone dihydrochloride monohydrate (2.00 g, 11.2 mmol) was dissolved in refluxing methanol and O-phenylmethylhydroxylamine hydrochloride (3.30 g, 20.5 mmol) was added. After refluxing for 20 hours the solvent was evaporated. The crude product was dissolved in methanol and an excess of trimethylorthoformate was added to the reaction mixture which was heated to reflux. After 48 hours the solvent was removed in vacuo. Crystallization from methanol/ethyl acetate afforded 1.60 g (60%) of white material. Mp. 167.5° C.

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 20 hours the solvent
  3. customwas evaporated
  4. dissolutionThe crude product was dissolved in methanol
  5. additionan excess of trimethylorthoformate was added to the reaction mixture which
  6. temperaturewas heated to reflux
  7. customAfter 48 hours the solvent was removed in vacuo
  8. customCrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-48bf23f6d68a4a0d9472c998f54b63b0
Source dataset
uspto-grants-1995_11
Patent number
US05470856

Linked notes

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