Dimethylcarbamoyl Chloride → HCID 14823092, compound

HRID 1073534Notes

Reaction equation

HRID 1073534 reaction equation
Cl.Cl.[C:3]([C:7]1[N:11]=[C:10]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[NH:9][N:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl.Cl.N1C=NC=N1.C(N(CC)CC)C.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:34][N:35]([CH3:39])[C:36]([N:9]1[C:10]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:11][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[N:8]1)=[O:37]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 22571451HCID 22571451, compoundHCID 178441979HCID 178441979, compound

Product 1

HCID 14823092HCID 14823092, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ten g of 3-t-butyl-5-(pyrid-2-yl-methylthio)-1H-1,2,4-triazole dihydrochloride, 0.5 g (4.1 mmole) of 1,2,4-triazole dihydrochloride, 0.5 g (4.1 mmole) of 4-dimethylaminopyridine, 10 g (100 mmole) of triethylamine, 3.5 g of dimethylcarbamoyl chloride and 100 ml of THF were refluxed for two hours. The mixture was concentrated in vacuo, and partitioned between ether and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and the solvent was removed in vacuo to yield 1-dimethylcarbamoyl-3-t-butyl-5-(pyrid-2-yl-methylthio)-1H-1,2,4triazole, an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between ether and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1282723b8a94477db8532dc636c187e9
Source dataset
uspto-grants-1990_11
Patent number
US04970224

Reaction notes

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