O,O-diethyl phosphorochloridothioate → 2-(Diethoxythiophosphoryloxy)-4-carbomethoxy-4,5,6,7-tetrahydrobenzothiazole

HRID 1288537Notes

Reaction equation

HRID 1288537 reaction equation
[C:1]([CH:5]1[C:10]2[NH:11][C:12](=[O:14])[S:13][C:9]=2[CH2:8][CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2].C(=O)([O-])N.[K+].[P:20](Cl)([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[S:21]>CC(C)=O>[CH2:23]([O:22][P:20]([O:14][C:12]1[S:13][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([C:1]([O:3][CH3:4])=[O:2])[C:10]=2[N:11]=1)([O:25][CH2:26][CH3:27])=[S:21])[CH3:24]

Participants

5

Reactant 3

HCID 17305O,O-diethyl phosphorochloridothioateHCID 21502757HCID 21502757, compoundHCID 23668002Potassium carbamate

Product 1

HCID 539910932-(Diethoxythiophosphoryloxy)-4-carbomethoxy-4,5,6,7-tetrahydrobenzothiazoleYield 21.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4 g of 4-carbomethoxy-2,3,4,5,6,7-hexahydrobenzothiazoline-2-one, 3 g of potassium carbamate and 50 ml of acetone was refluxed for 1 hour and after the addition of 4 g of O,O-diethyl chlorothiophosphate, the mixture was refluxed for another hour. The mixture was stirred for 18 hours at room temperature 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 an 8-2 cyclohexane-ethyl acetate mixture yielded 1.5 g of 2-(diethoxythiophosphoryloxy)-4-carbomethoxy-4,5,6,7-tetrahydrobenzothiazole with a refractive index nD26 = 1.5261.

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 an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-8678139bcb7e41f785c79727aa48c808
Source dataset
uspto-grants-1976_10
Patent number
US03988444

Reaction notes

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