Water → 1-(Diethylcarbamoyl)-3-(2-chloro-4-trifluoromethylphenylsulfonyl)-1,2,4-triazole

HRID 1885813Notes

Reaction equation

HRID 1885813 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([C:15]1[N:19]=[CH:18][NH:17][N:16]=1)(=[O:14])=[O:13].[CH2:20]([N:22]([CH2:26][CH3:27])[C:23](Cl)=[O:24])[CH3:21].O>N1C=CC=CC=1>[CH2:20]([N:22]([CH2:26][CH3:27])[C:23]([N:17]1[CH:18]=[N:19][C:15]([S:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[Cl:1])(=[O:14])=[O:13])=[N:16]1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6916Diethylcarbamoyl chlorideHCID 178527383HCID 178527383, compound

Product 1

HCID 538502441-(Diethylcarbamoyl)-3-(2-chloro-4-trifluoromethylphenylsulfonyl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(2-Chloro-4-trifluoromethylphenylsulfonyl)-1,2,4-triazole (3.12 g) and diethyl carbamoyl chloride (1.62 g) are dissolved in pyridine (10 ml) and reaction is performed at 50° C. for 5 h. After completion of the reaction, water (50 ml) is added to the reaction solution and the reaction product is extracted twice with ethyl acetate (100 ml). The ethyl acetate layer is washed first with 1N HCl, then with water, and subsequently dried with magnesium sulfate. The dried product is concentrated to form a crystal. Recrystallization from benzene/n-hexane produces the titled compound, 1-(diethylcarbamoyl)-3-(2-chloro-4-trifluoromethylphenylsulfonyl)-1,2,4-triazole, in an amount of 3.80 g; yield, 92.5%; m.p. 105.5°-107° C.

Workup

  1. customreaction
  2. additionis added to the reaction solution
  3. extractionthe reaction product is extracted twice with ethyl acetate (100 ml)
  4. washThe ethyl acetate layer is washed first with 1N HCl
  5. dry with materialwith water, and subsequently dried with magnesium sulfate
  6. concentrationThe dried product is concentrated
  7. customto form a crystal
  8. customRecrystallization from benzene/n-hexane

Sources & evidence

ORD record
ord-7ef3a89e028b44f88fc845f0ab165b57
Source dataset
uspto-grants-1992_09
Patent number
US05147445

Reaction notes

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