Ethanol → 2-[(6-methyl-4-oxo-1H-pyrimidin-2-yl)sulfanyl]acetamide

HRID 1605238Notes

Reaction equation

HRID 1605238 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]1[NH:12][C:11](=[S:13])[NH:10][C:9](=[O:14])[CH:8]=1.Cl[CH2:16][C:17]([NH2:19])=[O:18].C(O)C>O>[OH:14][C:9]1[CH:8]=[C:7]([CH3:6])[N:12]=[C:11]([S:13][CH2:16][C:17]([NH2:19])=[O:18])[N:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 667493Methylthiouracil

Product 1

HCID 1784295362-[(6-methyl-4-oxo-1H-pyrimidin-2-yl)sulfanyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 16.8 g. (0.2 mole) of sodium bicarbonate in 300 ml of water was added 22.8 g.(0.2 mole) of 6-methyl-2-thiouracil. The mixture was heated on a steam bath for 10 minutes. To this mixture was then added 18.6 g.(0.2 mole) of 2-chloroacetamide followed by 100 ml of absolute ethanol. The mixture was heated on a steam bath for 2 hours. The solution was cooled in an ice bath and the precipitate which formed was collected and recrystallized from a mixture of N,N-dimethylformamide and ethanol to afford 8 g. of product, m.p. 238°-240° d.

Workup

  1. temperatureThe mixture was heated on a steam bath for 10 minutes
  2. additionTo this mixture was then added 18.6 g
  3. temperatureThe mixture was heated on a steam bath for 2 hours
  4. temperatureThe solution was cooled in an ice bath
  5. customthe precipitate which formed
  6. customwas collected
  7. customrecrystallized from a mixture of N,N-dimethylformamide and ethanol
  8. customto afford 8 g

Sources & evidence

ORD record
ord-eb47cb79e7614aabb6349f98472e05d1
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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