Diethyl Ether → HCID 86734471, compound

HRID 435994Notes

Reaction equation

HRID 435994 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCOCC>C(N(CC)CC)C>[C:9]1([S:15]([C:5]2[NH:1][N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7369Benzenesulfonyl chlorideHCID 178513825HCID 178513825, compound

Product 1

HCID 86734471HCID 86734471, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a cooled, stirred mixture of 3 g. of 1,2,4-triazole-3-carboxamide and 4.8 g. of benzenesulfonyl chloride in 125 ml. of anhydrous ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 17.5 hours. The heterogeneous mixture is filtered and the colorless solid washed successively with ether, cold water and ether again, then air dried for approximately 10 minutes and dried in vacuo for 6 hours. The dried product is extracted with about 50 ml. of hot, dry acetonitrile then concentrated to about 25 ml. by water pump evacuation. The mixture is heated to redissolve the colorless crystalline solids which is again separated on cooling to room temperature. The solid is collected and washed with acetonitrile then dried in vacuo overnight, m.p. 150° -153° C.

Workup

  1. additionmixture of 3 g
  2. customThe cooling bath is removed
  3. stirringthe mixture is stirred at room temperature for 17.5 hours
  4. filtrationThe heterogeneous mixture is filtered
  5. washthe colorless solid washed successively with ether, cold water and ether again
  6. customair dried for approximately 10 minutes
  7. customdried in vacuo for 6 hours
  8. extractionThe dried product is extracted with about 50 ml
  9. concentrationof hot, dry acetonitrile then concentrated to about 25 ml
  10. temperatureThe mixture is heated
  11. dissolutionto redissolve the colorless crystalline solids which
  12. customis again separated
  13. customThe solid is collected
  14. washwashed with acetonitrile
  15. customthen dried in vacuo overnight, m.p. 150° -153° C.

Sources & evidence

ORD record
ord-995275021dde48eb8640b4c184e8df05
Source dataset
uspto-grants-1977_02
Patent number
US04007198

Reaction notes

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