Dimethylcarbamoyl Chloride → HCID 18998869, compound

HRID 2260654Notes

Reaction equation

HRID 2260654 reaction equation
[OH:1][C:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][S:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23]>C(#N)C.O>[CH3:20][N:21]([CH3:25])[C:22](=[O:23])[O:1][C:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][S:4][N:3]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 178519024HCID 178519024, compound

Product 1

HCID 18998869HCID 18998869, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In acetonitrile were suspended 0.80 g of 3-hydroxy-4-phenoxy-1,2,5-thiadiazole and 0.46 g of potassium carbonate and after adding 0.36 g of dimethylcarbamoyl chloride to the suspension, the mixture was refluxed for 12 hours. After allowing to cool, the reaction mixture was poured in water and extracted with ether. The ether layer was washed twice each time with a diluted aqueous solution of sodium hydroxide, water, and then a saturated aqueous sodium chloride solution. The ether layer thus washed was dried with anhydrous magnesium sulfate, concentrated, and thereafter purified by silica gel column chromatography to provide 0.85 g of 3-phenoxy-1,2,5-thiadiazol-4-yl N,N-dimethylcarbamate.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperatureto cool
  3. extractionextracted with ether
  4. washThe ether layer was washed twice each time with a diluted aqueous solution of sodium hydroxide, water
  5. washThe ether layer thus washed
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec9cc08ceb174d03ac1aeaa14bcd55b5
Source dataset
uspto-grants-1995_12
Patent number
US05478849

Reaction notes

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