Hydrochloric Acid → HCID 178423913, compound

HRID 1599037Notes

Reaction equation

HRID 1599037 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C[O-].[Na+].C([O:10][C:11](=O)[CH:12]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[C:13](OCC)=[O:14])C.Cl>CO.O>[OH:10][C:11]1[C:12]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:13]([OH:14])[N:4]=[C:2]([SH:3])[N:1]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 570878Diethyl 2-(p-tolyl)malonateHCID 2723790ThioureaHCID 10942334Sodium Methoxide

Product 1

HCID 178423913HCID 178423913, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of thiourea (13.69 g) in methanol (150 ml) is added a 28% solution of sodium methoxide in methanol (34.70 g) at 60° C., and thereto is further added (4-methylphenyl)malonic acid diethyl ester (32.62 g) at the same temperature. The reaction solution is refluxed for 8 hours. After cooling, water is added to the reaction solution, and the pH value of the solution is adjusted to pH 1 with hydrochloric acid under ice-cooing. The precipitated crystals are collected by filtration, and the residue is washed and dried to give 4,6-dihydroxy-2-mercapto-5-(4-methylphenyl)pyrimidine (12.53 g) as a crystal.

Workup

  1. temperatureThe reaction solution is refluxed for 8 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystals are collected by filtration
  4. washthe residue is washed
  5. customdried

Sources & evidence

ORD record
ord-a2c8b62d112441008f6e58411e6a34ab
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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