Dimethylcarbamoyl Chloride → HCID 19893974, compound

HRID 892743Notes

Reaction equation

HRID 892743 reaction equation
[C:1]([C:5]1N=C(SCC2OCCO2)[NH:7][N:6]=1)(C)(C)C.[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20].C([N:25](CC)CC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:17][N:18]([CH3:22])[C:19]([N:25]1[CH:1]=[CH:5][N:6]=[N:7]1)=[O:20]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178441981HCID 178441981, compound

Product 1

HCID 19893974HCID 19893974, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-t-Butyl-5-(1,3-dioxolan-2-yl-methylthio)-1H-1,2,4-triazole (7 g, 28.8 mmole), 2.8 ml (30.5 mmole) of dimethylcarbamoyl chloride, 8 ml (57 mmole) of triethylamine and 0.5 g (4.1 mmole) of 4-dimethylaminopyridine were dissolved in 50 ml of tetrahydrofuran (THF). The mixture was refluxed for four hours, concentrated in vacuo and partitioned between methylene chloride and dilute hydrochloric acid. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Chromatography on silica gel using ethyl ether/hexane gave 1-dimethylcarbamoyltriazole, an oil.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. concentrationconcentrated in vacuo
  3. custompartitioned between methylene chloride and dilute hydrochloric acid
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-596a5263ad334b0fa5bbb5dc584250bc
Source dataset
uspto-grants-1992_06
Patent number
US05120745

Reaction notes

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