Dimethylcarbamoyl Chloride → HCID 15346232, compound

HRID 1109244Notes

Reaction equation

HRID 1109244 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([S:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19].C(N(CC)CC)C>O1CCCC1>[CH3:16][N:17]([CH3:21])[C:18]([N:7]1[C:8]([S:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=[N:9][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6]1)=[O:19]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178441988HCID 178441988, compound

Product 1

HCID 15346232HCID 15346232, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g (8.0 mmle) of 3-t-butyl-5-(methylsulfonylmethylthio)-1H-1,2,4-triazole, 0.8 ml (8.8 mmole) of dimethyl carbamoyl chloride, 1.25 ml (9.0 mmole) of triethylamine and 0.1 g (0.8 mmole) of 4-dirmthylaminopyridine were dissolved in 20 ml of tetrahydrofuran and refluxed for 4 hours. After removal of the solvent the mixture was partitioned between ether and water, dried over magnesium sulfate and concentrated under vaccum. After chromatography on silica gel, trituration with ether afforded 1.4 g of 1-dimethylcarbamoYl-3-t-butyl-5-(methyl-sulfonylmethylthio)-1H-1,2,4-triazole. m.p. 109°-110° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. customAfter removal of the solvent the mixture
  3. customwas partitioned between ether and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vaccum

Sources & evidence

ORD record
ord-b92bd5b424834da89d632eb92b4d5e48
Source dataset
uspto-grants-1994_06
Patent number
US05319092

Reaction notes

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