Dimethylcarbamoyl Chloride → Triazamate

HRID 1109241Notes

Reaction equation

HRID 1109241 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:17][N:18]([CH3:22])[C:19]([N:7]1[C:8]([S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6]1)=[O:20]

Participants

5

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 178473166HCID 178473166, compound

Product 1

HCID 86306TriazamateYield 85.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 100 g (0.411 mole) of 3-t-butyl-5-carboethoxymethylthio-1H-1,2,4-triazole, 6 g (0.05 mole) of 4-dimethylaminopyridine, and 200 ml of pyridine was added 54 g (0.50 mole) of dimethylcarbamoyl chloride. The resulting solution was refluxed for eight hours and allowed to cool overnight. The reaction mixture was concentrated under vacuum, partitioned between ether and dilute hydrochloric acid. The organic layer was washed with water, brine, dried over magnesium sulfate, and concentrated under vacuum. Distillation yielded a fraction boiling at 148°-160° C at 0.1 torr 100 g (0.35 mole) of 1-dimethylcarbamoyl-3-t-butyl-5-carboethoxymethylthio-1,2,4-triazole. m.p. 55° C.

Workup

  1. temperatureThe resulting solution was refluxed for eight hours
  2. temperatureto cool overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. custompartitioned between ether and dilute hydrochloric acid
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. distillationDistillation

Sources & evidence

ORD record
ord-b1b9d5fb2a3940febd037c8ddf22f2ab
Source dataset
uspto-grants-1994_06
Patent number
US05319092

Reaction notes

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