Potassium Carbonate → HCID 21502749, compound

HRID 1288531Notes

Reaction equation

HRID 1288531 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[NH:3][C:2]1=[O:10].C(=O)([O-])[O-].[K+].[K+].[P:17](Cl)([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[S:18]>CC(C)=O>[CH2:20]([O:19][P:17]([O:10][C:2]1[S:1][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=1)([O:22][CH2:23][CH3:24])=[S:18])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 217932654,5,6,7-Tetrahydro-1,3-benzothiazol-2(3H)-one

Product 1

HCID 21502749HCID 21502749, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.2 g of 2,3,4,5,6,7-hexahydrobenzothiazoline-2-one, 8.4 g of potassium carbonate and 300 ml of acetone was refluxed for 1 hour and after the addition of 11.4 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 was filtered to remove mineral salts. The filtrate was concentrated to dryness by distillation under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 cyclohexane-ethyl acetate mixture yielded 7.3 g of 2-(diethoxythiophosphoryloxy)-4,5,6,7-tetrahydrobenzothiazole having a refractive index of nD22 = 1.532.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturethe mixture was refluxed for another hour
  3. filtrationwas filtered
  4. customto remove mineral salts
  5. concentrationThe filtrate was concentrated to dryness by distillation under reduced pressure
  6. customthe residue was chromatographed over silica gel
  7. washElution with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-7987a441840e4d0399024061a7e68716
Source dataset
uspto-grants-1976_10
Patent number
US03988444

Reaction notes

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