Sulfuric Acid → HCID 21153872, compound

HRID 2059214Notes

Reaction equation

HRID 2059214 reaction equation
[C:1]1([CH:7]([CH2:10][NH2:11])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:12]([OH:16])([OH:15])(=[O:14])=[O:13].CS[C:19](=N)[NH2:20].OS(O)(=O)=O>>[S:12]([OH:16])([OH:15])(=[O:14])=[O:13].[NH2:20][C:19]1[NH:11][CH2:10][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][N:9]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 752702-Methyl-2-thiopseudourea sulfateHCID 5687002-Phenyl-1,3-propanediamine

Product 1

HCID 21153872HCID 21153872, compoundYield 51.3%

Conditions

Temperature
265 °C

Procedure

A stirred mixture consisting of 3.25 g of 2-phenyl-1,3-propanediamine (prepared in accordance with Preparation C) and 3.02 g of 2-methyl-2-thiopseudourea sulfate ([CH3SC(NH)NH2 ]2.H2SO4) in a small flask is immersed in a 245° C. oil bath. The temperature is raised to 265° C. when the reaction mixture solidifies. When the reaction mixture melts again, it is stirred for about five minutes then is removed from the oil-bath. The contents are refluxed with 50 ml of methanol until a powder is formed. The mixture is cooled and the solid product is collected on a Buchner-funnel, washed with 30% ether in methanol and is air-dried to give 3.7 g of crude product. Recrystallization from 20 ml of water yields 2.25 g of 2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine sulfate, mp 264°-267° C.

Workup

  1. customthen is removed from the oil-bath
  2. temperatureThe contents are refluxed with 50 ml of methanol until a powder
  3. customis formed
  4. temperatureThe mixture is cooled
  5. customthe solid product is collected on a Buchner-funnel
  6. washwashed with 30% ether in methanol
  7. customis air-dried
  8. customto give 3.7 g of crude product
  9. customRecrystallization from 20 ml of water

Sources & evidence

ORD record
ord-e681faa2755044c5a1028aa347fd270f
Source dataset
uspto-grants-1982_03
Patent number
US04322421

Reaction notes

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