Dimethylcarbamoyl Chloride → 2,1-Benzothiazol-4-yl dimethylcarbamate

HRID 1973399Notes

Reaction equation

HRID 1973399 reaction equation
[OH:1][C:2]1[C:7]2=[CH:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>O.CN(C)C=O>[CH3:15][N:16]([CH3:20])[C:17](=[O:18])[O:1][C:2]1[C:7]2=[CH:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 13579433756911-04-7HCID 178418361HCID 178418361, compound

Product 1

HCID 214914402,1-Benzothiazol-4-yl dimethylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g. 4-hydroxy-2,1-benzisothiazole and 20 ml. dimethylformamide was added 0.4 g. of a 57 percent oil dispersion of sodium hydride at room temperature. After evolution of hydrogen from the mixture was completed, 1.1 g. dimethylcarbamoyl chloride was added and the mixture was stirred 16 hours at room temperature. Water (50 ml.) was added to the mixture, which was then extracted with chloroform. The chloroform extract was washed once with water and dried over calcium sulfate. Calcium sulfate was removed by filtration, and chloroform and dimethylformamide were evaporated from the filtrate in vacuo to give an oily residue. This was washed with hexane to give oily 2,1-benzisothiazol-4-yl N,N-dimethylcarbamate. This structure was confirmed by nmr. The insecticidal activity of this material was determined exactly as described in Example 12, whereby 2,1-benzisothiazole-4-yl N,N-dimethylcarbamate (500 ppm. concentration) destroyed 100 percent of bean aphides, two of five two-spotted mites, and had no effect on southern armyworms and Mexican bean beetle larvae.

Workup

  1. customat room temperature
  2. extractionwas then extracted with chloroform
  3. extractionThe chloroform extract
  4. washwas washed once with water
  5. dry with materialdried over calcium sulfate
  6. customCalcium sulfate was removed by filtration, and chloroform and dimethylformamide
  7. customwere evaporated from the filtrate in vacuo
  8. customto give an oily residue
  9. washThis was washed with hexane

Sources & evidence

ORD record
ord-6cee7f1fbda648e7b6170774c21a4509
Source dataset
uspto-grants-1976_12
Patent number
US03997548

Reaction notes

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