Diethylcarbamoyl chloride → HCID 19877740, compound

HRID 1885816Notes

Reaction equation

HRID 1885816 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]([O:10][CH3:11])[C:3]=1[S:12][C:13]1[N:17]=[CH:16][NH:15][N:14]=1.[CH2:18]([N:20]([CH2:24][CH3:25])[C:21](Cl)=[O:22])[CH3:19]>N1C=CC=CC=1>[CH2:18]([N:20]([CH2:24][CH3:25])[C:21]([N:15]1[CH:16]=[N:17][C:13]([S:12][C:3]2[C:4]([O:10][CH3:11])=[C:5]([CH3:9])[C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[N:14]1)=[O:22])[CH3:19]

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 178490074HCID 178490074, compound

Product 1

HCID 19877740HCID 19877740, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(2,4,5-Trimethyl-6-methoxyphenylthio)-1,2,4-triazole (2.5 g) is dissolved in pyridine (60 ml) and diethyl carbamoyl chloride (1.4 g) is added dropwise to the solution. The mixture is stirred at room temperature for 1 h, then at 70° C. for 2 h. After distilling off pyridine, the residue is extracted with chloroform and dried with magnesium sulfate to obtain a crude product of 1-(diethylcarbamoyl)-3-(2,4,5-trimethyl-6-methoxyphenylthio)-1,2,4-triazole. This crude product is cooled to 0° C. and m-chloroperbenzoic acid (4 g) is added, followed by stirring at room temperature for 2 h and at 60° C. for 2 h. Subsequently, 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 from n-hexane/ethyl acetate; yield, 2.6 g (74%); m.p. 138°-139° C.

Workup

  1. waitat 70° C. for 2 h
  2. distillationAfter distilling off pyridine
  3. extractionthe residue is extracted with chloroform
  4. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-3ff7509668d0438d9a7394a89cdbfb27
Source dataset
uspto-grants-1992_09
Patent number
US05147445

Reaction notes

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