Dimethylcarbamoyl Chloride → HCID 13020642, compound

HRID 971622Notes

Reaction equation

HRID 971622 reaction equation
[C:1]([C:5]1[NH:9][C:8]([S:10][CH2:11][CH:12]=[CH2:13])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][N:15]([CH3:19])[C:16](Cl)=[O:17]>N1C=CC=CC=1>[CH3:14][N:15]([CH3:19])[C:16]([N:7]1[C:8]([S:10][CH2:11][CH:12]=[CH2:13])=[N:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6]1)=[O:17]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 178460818HCID 178460818, compound

Product 1

HCID 13020642HCID 13020642, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 56 g (0.284 mol) of 3-tert.butyl-5-allylthio-4H-1,2,4-triazole and 31.2 g (0.29 mol) of dimethylcarbamyl chloride in 300 ml of pyridine was maintained at reflux temperature for 16 hrs. After the pyridine was removed at reduced pressure on the rotary evaporator, water was added followed by chloroform. The organic layer was washed with successive portions of dilute hydrochloric acid, water and brine, then dried over Na2SO4. The solvent was removed in vacuo to give 66.3 g of an oil, nD26 1.5126.

Workup

  1. temperatureat reflux temperature for 16 hrs
  2. customAfter the pyridine was removed at reduced pressure on the rotary evaporator, water
  3. additionwas added
  4. washThe organic layer was washed with successive portions of dilute hydrochloric acid, water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3ffe259a337d4d22b151de413280850e
Source dataset
uspto-grants-1979_07
Patent number
US04160839

Reaction notes

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