Diethyl Ether → HCID 178446997, compound

HRID 435737Notes

Reaction equation

HRID 435737 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].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:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 62493Pivaloyl chlorideHCID 178513825HCID 178513825, compound

Product 1

HCID 178446997HCID 178446997, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 3.4 g. of pivaloyl 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 24 hours. The off-white solid is collected by filtration and washed thoroughly with diethyl ether and then cold water. The ether-cold water filtrate deposits another solid almost immediately. This solid is collected by filtration and dried in vacuo for 3.5 hours, yielding 0.22 g. This 0.22 g. is extracted with hot, dry acetonitrile. Concentration of the acetonitrile filtrate to a very small volume gives a colorless, crystalline solid which is collected, washed with a small amount of acetonitrile and dried in vacuo for 2 hours, yielding 50 mg., m.p. 132°-140° C. (dec.).

Workup

  1. additionmixture of 3 g
  2. customThe cooling bath is removed
  3. stirringthe mixture is stirred at room temperature for 24 hours
  4. filtrationThe off-white solid is collected by filtration
  5. washwashed thoroughly with diethyl ether
  6. filtrationThis solid is collected by filtration
  7. customdried in vacuo for 3.5 hours
  8. customyielding 0.22 g
  9. extractionis extracted with hot, dry acetonitrile
  10. customConcentration of the acetonitrile filtrate to a very small volume gives a colorless, crystalline solid which
  11. customis collected
  12. washwashed with a small amount of acetonitrile
  13. customdried in vacuo for 2 hours
  14. customyielding 50 mg

Sources & evidence

ORD record
ord-bd78795076364614995cc05dcf141878
Source dataset
uspto-grants-1977_02
Patent number
US04006159

Reaction notes

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