Diethyl Ether → HCID 178513855, compound

HRID 435733Notes

Reaction equation

HRID 435733 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.[C:9]12([C:19](Cl)=[O:20])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.C(OCC)C>C(N(CC)CC)C>[C:9]12([C:19]([C:5]3[NH:1][N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=3)=[O:20])[CH2:16][CH:15]3[CH2:14][CH:13]([CH2:12][CH:11]([CH2:17]3)[CH2:10]1)[CH2:18]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 989151-Adamantanecarbonyl chlorideHCID 178513825HCID 178513825, compound

Product 1

HCID 178513855HCID 178513855, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a cooled, stirred mixture of 2 g. of 1,2,4-triazole-3-carboxamide and 5.4 g. of adamantylcarbonyl 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 23.5 hours. The mixture is filtered and the solid is washed successively with diethyl ether, cold water, diethyl ether and dried in vacuo for 3 hours yielding 4.5 g. of colorless solid. This solid is extracted with hot dry acetonitrile, cooled and washed with acetonitrile yielding 0.4 g. of colorless crystals. The remaining 3.5 g. of acetonitrile insoluble solid is further extracted with acetonitrile, yielding an additional 0.6 g. of product, m.p. 213°-216° C. (dec.).

Workup

  1. additionmixture of 2 g
  2. customThe cooling bath is removed
  3. stirringthe mixture is stirred at room temperature for 23.5 hours
  4. filtrationThe mixture is filtered
  5. washthe solid is washed successively with diethyl ether, cold water, diethyl ether
  6. customdried in vacuo for 3 hours
  7. customyielding 4.5 g
  8. extractionThis solid is extracted with hot dry acetonitrile
  9. temperaturecooled
  10. washwashed with acetonitrile yielding 0.4 g
  11. extractionof acetonitrile insoluble solid is further extracted with acetonitrile
  12. customyielding an additional 0.6 g

Sources & evidence

ORD record
ord-a3e30299317346bc8fdfcfb9e9ce1dae
Source dataset
uspto-grants-1977_02
Patent number
US04006159

Reaction notes

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