Diethyl Ether → HCID 178513856, compound

HRID 435732Notes

Reaction equation

HRID 435732 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C>C(N(CC)CC)C>[C:9]([C:5]1[NH:1][N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 178513825HCID 178513825, compound

Product 1

HCID 178513856HCID 178513856, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 4 g. of benzoyl chloride in 125 ml. of anhydrous diethyl ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 18 hours. The heterogeneous mixture is filtered and washed successively with diethyl ether, cold water and then diethyl ether and dried in vacuo for 4 hours yielding 4 g. of colorless solid. This solid is extracted with hot, dry acetonitrile and cooled yielding a solid product which is collected, washed with acetonitrile and dried in vacuo, yielding 1 g. of product, m.p. 174°-178° C. (dec.).

Workup

  1. additionmixture of 3 g
  2. customThe cooling bath is removed
  3. stirringthe mixture is stirred at room temperature for 18 hours
  4. filtrationThe heterogeneous mixture is filtered
  5. washwashed successively with diethyl ether, cold water
  6. dry with materialdiethyl ether and dried in vacuo for 4 hours
  7. customyielding 4 g
  8. extractionThis solid is extracted with hot, dry acetonitrile
  9. temperaturecooled
  10. customyielding a solid product which
  11. customis collected
  12. washwashed with acetonitrile
  13. customdried in vacuo
  14. customyielding 1 g

Sources & evidence

ORD record
ord-e4c6ea2d9e674d2983f5810dca5bdca4
Source dataset
uspto-grants-1977_02
Patent number
US04006159

Reaction notes

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