Methyl iodide → 6945-56-8

HRID 261787Notes

Reaction equation

HRID 261787 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][O-].[Na+].C([O:11][C:12](=O)[CH2:13][C:14]([O:16]CC)=O)C.CI>CO>[OH:11][C:12]1[N:5]=[C:3]([S:4][CH3:6])[N:2]([CH3:1])[C:14](=[O:16])[CH:13]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7761Diethyl MalonateHCID 2723704MethylthioureaHCID 10942334Sodium Methoxide

Product 1

HCID 1354085986945-56-8Yield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 45 g (0.5 mol) of N-methylthiourea, 54 g (1 mol) of sodium methylate, 200 ml of methanol and 80 g (0.5 mol) of malonic acid diethyl ester was boiled for 3 hours under reflux. 71 g (0.5 mol) of methyl iodide were then added dropwise at about 50° C. and the mixture was stirred for a further 0.5 hour at 50° C. The salt which crystallized out was filtered off and was then dissolved in 400 ml of water. The solution was neutralized by adding glacial acetic acid, the precipitate was then filtered off, and 80 g (93% of theory) of 1,6-dihydro-4-hydroxy-1-methyl-2-methylthio-6-oxo-pyrimidine were thus obtained in the form of a colorless powder of melting point 198° C.

Workup

  1. temperatureunder reflux
  2. customThe salt which crystallized out
  3. filtrationwas filtered off
  4. dissolutionwas then dissolved in 400 ml of water
  5. additionby adding glacial acetic acid
  6. filtrationthe precipitate was then filtered off

Sources & evidence

ORD record
ord-bc050518ce3f4da0931d72669a3be481
Source dataset
uspto-grants-1979_05
Patent number
US04152426

Reaction notes

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