Methanethiol → HCID 178503663, compound

HRID 485478

Reaction equation

HRID 485478 reaction equation
C1(C)C=CC(S(O[CH2:11][C:12]#[N:13])(=O)=O)=CC=1.C[O-].[Na+].[Cl-].[NH4+:19].[CH3:20][SH:21].[CH3:22][CH:23]([C:28]([CH3:30])=O)[C:24](OC)=[O:25]>CO>[CH3:20][S:21][CH2:11][C:12]1[N:13]=[C:24]([OH:25])[C:23]([CH3:22])=[C:28]([CH3:30])[N:19]=1

Participants

7

Reactant 5

HCID 878MethanethiolHCID 25517Ammonium ChlorideHCID 84525Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)-HCID 86508Methyl 2-methylacetoacetateHCID 10942334Sodium Methoxide3×

Product 1

HCID 178503663HCID 178503663, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

21.1 g (0.1 mol) of cyanomethyl p-toluenesulphonate are added in portions to a solution of 0.01 mol of sodium methylate in 100 ml of methanol at 0° to 5° C. The mixture is allowed to come to 20° C., 5.9 g (0.11 mol) of ammonium chloride are added at this temperature and the mixture is stirred at room temperature for 4 hours. 6 g (0.125 mol) of methylmercaptan are then passed in at 10° C., a solution of 0.11 mol sodium methylate in 20 ml of methanol is added dropwise at the same temperature, and the mixture is stirred first at 0° to 5° C. for 1 hour and then without cooling for 2 hours. A further 0.22 mol of sodium methylate in 40 ml of methanol and then 13 g (0.1 mol) of methyl 2-methylacetoacetate are added to the reaction mixture at room temperature, and the mixture is subsequently stirred at room temperature for a further 18 hours. The solvent is then distilled off in vacuo, the residue is dissolved in 100 ml of water and the solution is brought to pH 4 with concentrated hydrochloric acid at 10° to 20° C. The product which has precipitated is filtered off with suction and rinsed with 20 ml of cold water. 12.8 g (70% of theory) of 2-methylthiomethyl-4-hydroxy-5,6-dimethylpyrimidine are obtained in this manner in the form of a beige powder of melting point 166° C.

Workup

  1. customto come to 20° C.
  2. customare then passed in at 10° C.
  3. stirringthe mixture is stirred first at 0° to 5° C. for 1 hour
  4. temperaturewithout cooling for 2 hours
  5. stirringthe mixture is subsequently stirred at room temperature for a further 18 hours
  6. distillationThe solvent is then distilled off in vacuo
  7. dissolutionthe residue is dissolved in 100 ml of water
  8. customis brought to pH 4 with concentrated hydrochloric acid at 10° to 20° C
  9. customThe product which has precipitated
  10. filtrationis filtered off with suction
  11. washrinsed with 20 ml of cold water

Sources & evidence

ORD record
ord-d872539e68ae49b29214070766a6f840
Source dataset
uspto-grants-1985_08
Patent number
US04536574

Linked notes

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