Dimethylcarbamoyl Chloride → HCID 15346232, compound

HRID 129974Notes

Reaction equation

HRID 129974 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>CN(C)C1C=CN=CC=1.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

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178441988HCID 178441988, compound

Product 1

HCID 15346232HCID 15346232, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2 g (8.0 mmole) of 3-t-butyl-5-(methylsulfonylmethylthio)-1H-1,2,4-triazole, 0.8 ml (8.8 mmole) of dimethylcarbamoyl chloride, 1.25 ml (9.0 mmole) of triethylamine and 0.1 g (0.8 mmole) of 4-dimethylaminopyridine 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-(methylsulfonylmethylthio)-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-12a2f6167be0468892d17faed57816c1
Source dataset
uspto-grants-1995_11
Patent number
US05470984

Reaction notes

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