Dimethylcarbamoyl Chloride → HCID 13020642, compound

HRID 1395741Notes

Reaction equation

HRID 1395741 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-0e3645caab8a41d386afbc1a7d04136e
Source dataset
uspto-grants-1980_05
Patent number
US04205177

Reaction notes

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