Thiourea → HCID 178429718, compound

HRID 704491Notes

Reaction equation

HRID 704491 reaction equation
C([O:4][CH2:5][C:6]1[N:16]=[C:9]2[N:10]=[C:11]([CH3:15])[CH:12]=[C:13](Cl)[N:8]2[N:7]=1)(=O)C.NC(N)=[S:19]>C(O)C>[OH:4][CH2:5][C:6]1[N:16]=[C:9]2[N:10]=[C:11]([CH3:15])[CH:12]=[C:13]([SH:19])[N:8]2[N:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 156727342-Acetoxymethyl-7-chloro-5-methyl-s-triazolo[1,5-a]pyrimidine

Product 1

HCID 178429718HCID 178429718, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 400 ml of ethanol was dissolved 23.7 g of 2-acetoxymethyl-7-chloro-5-methyl-s-triazolo[1,5-a]pyrimidine, and 19 g of thiourea was added thereto and the mixture was stirred for 30 minutes under reflux. The reaction mixture was ice-cooled and the precipitated crystals were collected by filtration, washed with ethanol and dried. After the obtained crystals were dissolved in a 10% potassium hydroxide aqueous solution and stirred for 30 minutes, pH was adjusted to 2 with addition of a 2N hydrochloric acid. The precipitated crystals were collected by filtration, washed with water and dried to obtain 15.3 g of the title compound.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with ethanol
  6. customdried
  7. dissolutionAfter the obtained crystals were dissolved in a 10% potassium hydroxide aqueous solution
  8. stirringstirred for 30 minutes
  9. additionpH was adjusted to 2 with addition of a 2N hydrochloric acid
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-4ee966460beb41f8a96b658d2b034e01
Source dataset
uspto-grants-1991_01
Patent number
US04987129

Reaction notes

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