Sodium Hydroxide → HCID 53881579, compound

HRID 126781Notes

Reaction equation

HRID 126781 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([SH:10])[N:7]=[CH:6][N:5]=1.[C:11]1([CH3:21])C=CC(S([O-])(=O)=O)=CC=1.[CH2:22]([OH:24])C.O>>[NH2:3][C:4]1[CH:9]=[C:8]([S:10][CH2:21][CH2:11][O:24][CH3:22])[N:7]=[CH:6][N:5]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 85570p-ToluenesulfonateHCID 19096565Water ethanolHCID 178507973HCID 178507973, compound

Product 1

HCID 53881579HCID 53881579, compoundYield 80%

Conditions

Temperature
60 °C

Procedure

20 g of sodium hydroxide (0.5 mol) are dissolved in 500 ml of ethanol/water at 1:1. 63.5 g of 4-amino-6-mercaptopyrimidine (0.5 mol) are added to the solution and the temperature of the solution is brought to 60° C. 115 g of p-toluene sulphonate of β-methoxyethyl (0.5 mol) are added drop by drop over 30 minutes, maintaining the temperature at 60° C. with a water bath. The addition terminated, the reaction mixture is refluxed for three hours. Then the solvent is evaporated and the residue is recovered with 250 ml of water. The aqueous solution is repeatedly extracted with chloroform (6×100 ml) and the amalgamated extracts are evaporated until dry. The solid residue is crystallised from ethyl acetate plus petroleum ether. 74 g of product are obtained (80% yield) with a melting point of 78°-80° C.

Workup

  1. customis brought to 60° C
  2. additionThe addition
  3. customterminated
  4. temperaturethe reaction mixture is refluxed for three hours
  5. customThen the solvent is evaporated
  6. customthe residue is recovered with 250 ml of water
  7. extractionThe aqueous solution is repeatedly extracted with chloroform (6×100 ml)
  8. customthe amalgamated extracts are evaporated
  9. customuntil dry
  10. customThe solid residue is crystallised from ethyl acetate plus petroleum ether

Sources & evidence

ORD record
ord-af122c74738d4ba5a8549b22e02238bb
Source dataset
uspto-grants-1981_03
Patent number
US04254126

Reaction notes

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