Diethyl Ether → HCID 86734473, compound

HRID 435995Notes

Reaction equation

HRID 435995 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].CCOCC>C(N(CC)CC)C>[C:15]1([CH3:16])[CH:17]=[CH:18][C:12]([S:9]([C:5]2[NH:1][N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 178513825HCID 178513825, compound

Product 1

HCID 86734473HCID 86734473, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a cooled, stirred mixture of 3.0 g. of 1,2,4-triazole- 3-carboxamide and 5.1 g. of tosyl 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 23 hours. The heterogeneous mixture is filtered and washed successively with ether, cold water and then ether and dried in vacuo for 4.5 hours yielding a crude colorless solid. This solid is heated in about 50 ml. of acetonitrile and the hot mixture is filtered. The filtrate is concentrated to a smaller volume of about 20 ml. in vacuo. A colorless solid separates from the filtrate, which is collected and washed with acetonitrile and air dried for 10 minutes. The product is then dried overnight in vacuo, m.p. 148°-150° C.

Workup

  1. additionmixture of 3.0 g
  2. customThe cooling bath is removed
  3. stirringthe mixture is stirred at room temperature for 23 hours
  4. filtrationThe heterogeneous mixture is filtered
  5. washwashed successively with ether, cold water
  6. dry with materialether and dried in vacuo for 4.5 hours
  7. customyielding a crude colorless solid
  8. temperatureThis solid is heated in about 50 ml
  9. filtrationof acetonitrile and the hot mixture is filtered
  10. concentrationThe filtrate is concentrated to a smaller volume of about 20 ml
  11. customA colorless solid separates from the filtrate, which is collected
  12. washwashed with acetonitrile and air
  13. customdried for 10 minutes
  14. customThe product is then dried overnight in vacuo, m.p. 148°-150° C.

Sources & evidence

ORD record
ord-d2e7258e0c2d4d63aee63ce68a3d8549
Source dataset
uspto-grants-1977_02
Patent number
US04007198

Reaction notes

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