Dimethylamine → 1H-1,2,4-Triazole-1-carboxamide, 3-tert-butyl-N,N-dimethyl-5-(methylthio)-

HRID 27258Notes

Reaction equation

HRID 27258 reaction equation
[C:1]([C:5]1[NH:9][C:8]([S:10][CH3:11])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12](Cl)(Cl)=[O:13].[CH3:16][NH:17][CH3:18]>C1(C)C=CC=CC=1>[CH3:16][N:17]([CH3:18])[C:12]([N:7]1[C:8]([S:10][CH3:11])=[N:9][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6]1)=[O:13]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6371PhosgeneHCID 178503613HCID 178503613, compound

Product 1

HCID 30492461H-1,2,4-Triazole-1-carboxamide, 3-tert-butyl-N,N-dimethyl-5-(methylthio)-Yield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 5.0 g (0.029 m) of 3-tert.butyl-5-methylthio-1,2,4-4H-triazole in toluene (100 ml) was added 50 ml of a toluene solution of phosgene (12%) and the reaction was heated to reflux for 2 hrs. After cooling, an excess of aqueous dimethyl amine was added and, after stirring at room temperature for 1 hr. the organic phase was washed with dilute hydrochloric acid, then with water and was then dried over anhydrous sodium sulfate. The toluene was evaporated to near dryness at reduced pressure and the residue was crystallized from hexane. Filtration gave 6.1 g (87%) of 1-dimethylcarbamyl-3-tert.butyl-5-methylthio-1,2,4-1H-triazole, MP 51°-53° C. Spectral properties agree with the structure as represented above:

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hrs
  3. temperatureAfter cooling
  4. washthe organic phase was washed with dilute hydrochloric acid
  5. dry with materialwith water and was then dried over anhydrous sodium sulfate
  6. customThe toluene was evaporated
  7. customthe residue was crystallized from hexane
  8. filtrationFiltration

Sources & evidence

ORD record
ord-5204eb5f52a8431dab6c3ec5f20a242b
Source dataset
uspto-grants-1980_09
Patent number
US04220790

Reaction notes

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