Thiourea → HCID 178527722, compound

HRID 477537Notes

Reaction equation

HRID 477537 reaction equation
[NH2:1][C:2](N)=[S:3].[Cl:5][C:6]1[CH:11]=C(Cl)N2[N:13]=[CH:14][N:15]=[C:8]2[N:7]=1>C(O)C>[Cl:5][C:6]1[CH:11]=[C:2]([SH:3])[N:1]2[N:13]=[CH:14][N:15]=[C:8]2[N:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 134918375,7-Dichloro[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 178527722HCID 178527722, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (1.7 g) was added all at once to a solution of 4.2 g of 5,7-dichloro-s-triazolo[1,5-a]pyrimidine in 140 ml anhydrous ethanol at room temperature, the mixture was refluxed for 30 minutes, the crystals formed upon ice cooling were filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 18 ml of 1N sodium hydroxide solution. The resulting solution was washed with 20 ml of ethyl acetate. The pH was adjusted to 1.0 with concentrated hydrochloric acid to give crystals. The crystals were collected by filtration and washed with 20 ml of water and then with 20 ml of methanol, affording 1.2 g of the objective compound as faint yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. customthe crystals formed upon ice cooling
  3. filtrationwere filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 18 ml of 1N sodium hydroxide solution
  6. washThe resulting solution was washed with 20 ml of ethyl acetate
  7. customto give crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed with 20 ml of water

Sources & evidence

ORD record
ord-48f3d357d52d469f8f42020647f68ca1
Source dataset
uspto-grants-1989_12
Patent number
US04888332

Reaction notes

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