Diethyl Ether → HCID 178443061, compound

HRID 435736Notes

Reaction equation

HRID 435736 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.[C:9](Cl)(=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].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:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8206Palmitoyl chlorideHCID 178513825HCID 178513825, compound

Product 1

HCID 178443061HCID 178443061, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 7.4 g. of palmitoyl 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 mixture is filtered and the solid is washed successively with diethyl ether, cold water, diethyl ether and then dried in vacuo for 4 hours. The solid is extracted with hot dry acetonitrile and cooled yielding a colorless solid. The solid is redissolved by heating the mixture and allowed to recrystallize from the clear, colorless solution. The product is collected, washed with acetonitrile and dried in vacuo for 3 hours, yielding 0.75 g., m.p. 145°-160° C. (dec.).

Workup

  1. additionmixture of 3 g
  2. customThe cooling bath is removed
  3. stirringthe mixture is stirred
  4. filtrationThe mixture is filtered
  5. washthe solid is washed successively with diethyl ether, cold water, diethyl ether
  6. customdried in vacuo for 4 hours
  7. extractionThe solid is extracted with hot dry acetonitrile
  8. temperaturecooled
  9. customyielding a colorless solid
  10. dissolutionThe solid is redissolved
  11. temperatureby heating the mixture
  12. customto recrystallize from the clear, colorless solution
  13. customThe product is collected
  14. washwashed with acetonitrile
  15. customdried in vacuo for 3 hours
  16. customyielding 0.75 g

Sources & evidence

ORD record
ord-eb253d87ebf9409fa2b306268ce34938
Source dataset
uspto-grants-1977_02
Patent number
US04006159

Reaction notes

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