Potassium Carbonate → Phosphorothioic acid, O-(5,6-dihydro-4H-cyclopentathiazol-2-yl) O,O-diethyl ester

HRID 1288535Notes

Reaction equation

HRID 1288535 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[NH:3][C:2]1=[O:9].C(=O)([O-])[O-].[K+].[K+].[P:16](Cl)([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[S:17]>CC(C)=O>[CH2:19]([O:18][P:16]([O:9][C:2]1[S:1][C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[N:3]=1)([O:21][CH2:22][CH3:23])=[S:17])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 432867903,4,5,6-Tetrahydro-2H-cyclopenta[d][1,3]thiazol-2-one

Product 1

HCID 86734109Phosphorothioic acid, O-(5,6-dihydro-4H-cyclopentathiazol-2-yl) O,O-diethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 21 g of 2,3,5,6,-tetrahydro-4H-cyclopentathiazoline-2-one, 21 g of potassium carbonate and 300 ml of acetone was refluxed for 1 hour and after the addition of 28 g of O,O-diethyl chlorothiophosphate thereto, the mixture was refluxed for 1 hour. The mineral salts were filtered off and the filtrate was distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate to obtain 4g of 2-(diethoxythiophosphoryloxy)-5,6-dihydro-4H-cyclopentathiazole with a refractive index of nD28 = 1.5348.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturethe mixture was refluxed for 1 hour
  3. filtrationThe mineral salts were filtered off
  4. distillationthe filtrate was distilled to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with an 8-2 cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-d9a4820b77694722b8b35eecc1f22f65
Source dataset
uspto-grants-1976_10
Patent number
US03988444

Reaction notes

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