Potassium Carbonate → 2-(Diethoxythiophosphoryloxy)-4,5,6,7-tetrahydro-7-oxo-benzothiazole

HRID 1288533Notes

Reaction equation

HRID 1288533 reaction equation
[O:1]=[C:2]1[C:10]2[S:9][C:8](=[O:11])[NH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[P:18](Cl)([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[S:19]>CC(C)=O>[CH2:21]([O:20][P:18]([O:11][C:8]1[S:9][C:10]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=2[N:7]=1)([O:23][CH2:24][CH3:25])=[S:19])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 64245982-Hydroxy-5,6-dihydro-4H-benzothiazol-7-one

Product 1

HCID 539736922-(Diethoxythiophosphoryloxy)-4,5,6,7-tetrahydro-7-oxo-benzothiazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.4 g of 7-oxo-2,3,4,5,6,7-hexahydrobenzothiazoline-2-one, 10.5 g of potassium carbonate and 100 ml of acetone was refluxed for 1 hour and after addition of 14.5 g of O,O-diethyl chlorothiophosphate thereto, the mixture was refluxed for another hour. The mixture was stirred at room temperature for 24 hours and the mineral salts formed were filtered off. The filtrate was distilled to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 6 -4 cyclohexane-ethyl acetate mixture resulted in 3.5 g of 2-(diethoxythiophosphoryloxy)-4,5,6,7-tetrahydro-7-oxo-benzothiazole with a refractive index of nD20 = 1.555.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturethe mixture was refluxed for another hour
  3. customthe mineral salts formed
  4. filtrationwere filtered off
  5. distillationThe filtrate was distilled to dryness under reduced pressure
  6. customthe residue was chromatographed over silica gel
  7. washElution with a 6 -4 cyclohexane-ethyl acetate mixture
  8. customresulted in 3.5 g of 2-(diethoxythiophosphoryloxy)-4,5,6,7-tetrahydro-7-oxo-benzothiazole with a refractive index of nD20 = 1.555

Sources & evidence

ORD record
ord-1b07e0c5728e4aee85ac04ff9ba953e0
Source dataset
uspto-grants-1976_10
Patent number
US03988444

Reaction notes

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