HCID 3042017, compound → HCID 18919350, compound

HRID 1290815Notes

Reaction equation

HRID 1290815 reaction equation
[Cl:1][CH:2]=[CH:3][C:4](=O)[CH2:5]Cl.ClC=CC(=O)C(C)C.[NH2:16][C:17]1[N:21]=[CH:20][NH:19][N:18]=1>C(O)(=O)C>[Cl:1][CH2:2][C:3]1[N:18]2[N:19]=[CH:20][N:21]=[C:17]2[N:16]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3042017HCID 3042017, compoundHCID 53421801HCID 53421801, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 18919350HCID 18919350, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,4-Dichloro-1-buten-3-one (10.9 g) (prepared in a manner analogous to the preparation of 1-chloro-4-methyl-1-penten-3-one described in Example 20 below), 3-amino-1,2,4-triazole (6.5 g) and glacial acetic acid were heated under reflux for 1 hour and 30 minutes. The reaction mixture was poured onto ice and extracted with dichloromethane. The organic layer was dried over magnesium sulphate and the solvent was evaporated to give a solid. The crude product was purified by flash chromatography using as eluent a mixture of dichloromethane and ethanol (in the ratio 97:3 respectively), followed by recrystallisation from tetrachloromethane, to give 7-chloromethyl-1,2,4-triazolo[1,5-a]pyrimidine. Yield 10.15 g.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 1 hour and 30 minutes
  3. additionThe reaction mixture was poured onto ice
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. customthe solvent was evaporated
  7. customto give a solid
  8. customThe crude product was purified by flash chromatography
  9. additiona mixture of dichloromethane and ethanol (in the ratio 97:3 respectively),
  10. customfollowed by recrystallisation from tetrachloromethane

Sources & evidence

ORD record
ord-026c8a65562c4e2b93e9ac28749e2220
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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