Diethylcarbamoyl chloride → HCID 19877739, compound

HRID 1885815Notes

Reaction equation

HRID 1885815 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9][C:10]1[N:14]=[CH:13][NH:12][N:11]=1.[CH2:15]([N:17]([CH2:21][CH3:22])[C:18](Cl)=[O:19])[CH3:16]>N1C=CC=CC=1>[CH2:15]([N:17]([CH2:21][CH3:22])[C:18]([N:12]1[CH:13]=[N:14][C:10]([S:9][C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[N:11]1)=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 178424824HCID 178424824, compound

Product 1

HCID 19877739HCID 19877739, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(2,6-Dimethylphenylthio)-1,2,4-triazole (2 g) is dissolved in pyridine (50 ml) and diethyl carbamoyl chloride (1.4 g) is added dropwise to the solution. The mixture is stirred first at room temperature for 1 h, then at 70° C. for 2 h. Thereafter, pyridine is distilled off. The residue is extracted with chloroform and dried with magnesium sulfate to obtain the crude product of 1-(diethylcarbamoyl)-3-(2,6-dimethylphenylthio)-1,2,4-triazole. After cooling to 0° C., m-chloroperbenzoic acid (4 g) is added and the mixture is stirred at room temperature for 4 h. The resulting product is washed with a 10% aqueous solution of potassium carbonate and dried with magnesium sulfate. After distilling off the solvent, the residue is recrystallized with n-hexane/ethyl acetate; m.p. 111°-112° C.; yield, 2.4 g (72%).

Workup

  1. waitat 70° C. for 2 h
  2. distillationThereafter, pyridine is distilled off
  3. extractionThe residue is extracted with chloroform
  4. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-8d4f3b79e2254aceae5f5639d1d4d8c3
Source dataset
uspto-grants-1992_09
Patent number
US05147445

Reaction notes

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