Acetic Acid → HCID 178503447, compound

HRID 1605858Notes

Reaction equation

HRID 1605858 reaction equation
[OH-].[Na+].C([O:5][C:6](=O)[CH2:7][C:8]([CH3:10])=O)C.S(O)(O)(=O)=O.[CH3:17][S:18][C:19](=[NH:21])[NH2:20].C(O)(=O)C>O>[CH3:17][S:18][C:19]1[N:21]=[C:6]([OH:5])[CH:7]=[C:8]([CH3:10])[N:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 178503447HCID 178503447, compoundYield 188.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 120 g of sodium hydroxide (3 moles) in 250 ml of water was added dropwise at room temperature to a mixture of 195 g (1.5 moles) of acetoacetic acid ethyl ester, 210 g (0.76 mole) of S-methylisothiourea sulfate and 300 ml of water and the batch was allowed to react for a further 18 hours at room temperature. The reaction mixture was then acidified with acetic acid and the product which had crystallized out was filtered off and rinsed thoroughly with water. 224 g (96% of theory) of 2-methylmercapto-4-hydroxy-6-methyl-pyrimidine were obtained in the form of a colorless powder of melting point 219°C.

Workup

  1. customto react for a further 18 hours at room temperature
  2. customthe product which had crystallized out
  3. filtrationwas filtered off
  4. washrinsed thoroughly with water

Sources & evidence

ORD record
ord-9c8b66f0bcb04969938a2019c7f86a7b
Source dataset
uspto-grants-1976_04
Patent number
US03951975

Reaction notes

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