Phosphorus oxychloride → HCID 17604534, compound

HRID 1414096Notes

Reaction equation

HRID 1414096 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([CH3:11])[C:8](O)=O)=[CH:4][CH:3]=1.[NH2:14][NH:15][C:16]([NH2:18])=[S:17].P(Cl)(Cl)(Cl)=O>O1CCOCC1>[CH3:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([C:8]2[S:17][C:16]([NH2:18])=[N:15][N:14]=2)[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 2723789ThiosemicarbazideHCID 36436262-(4-methylphenoxy)propanoic acid

Product 1

HCID 17604534HCID 17604534, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A 100 milliliter flask adapted with a paddle stirrer, thermometer, addition funnel, condenser and drying tube was charged with 7.2 grams (0.040 mole) of 2-(4-methylphenoxy)propanoic acid, 3.6 grams (0.040 mole) of thiosemicarbazide and 30 milliliters of dioxane, and heated to 90° C. the addition funnel was charged with phosphorous oxychloride (POCl3), (6.7 grams, 0.4 mole) which was slowly added for 15 minutes while maintaining the temperature within 90°-95° C. When the addition was completed, the mixture was refluxed for 60 minutes. The flask was evacuated by using a water aspirator to remove volatiles (HCl, POCl3 and some dioxane), and then 50 milliliters of water was added and mixture was made basic by the addition of 50 percent solution of NaOH until the pH of the solution was 10. The white precipitate was filtered off, washed with water and dried in a vacuum oven at 80° C. to 7.7 grams of tan crystals (melting point 142°-162° C.) which were recrystallized from the minimum amount of a water ethanol mixture, filtered off and dried in a vacuum oven at 80° C. to 4.8 grams of yellow crystals of 5-[1-(4-methylphenoxy)ethyl]-2-amino-1,3,4-thiadiazole (melting point 178°-180° C.).

Workup

  1. customA 100 milliliter flask adapted with a paddle stirrer
  2. additionthermometer, addition funnel, condenser
  3. customdrying tube
  4. additionwas slowly added for 15 minutes
  5. temperaturewhile maintaining the temperature within 90°-95° C
  6. additionWhen the addition
  7. temperaturethe mixture was refluxed for 60 minutes
  8. customThe flask was evacuated
  9. customto remove volatiles (HCl, POCl3
  10. additionsome dioxane), and then 50 milliliters of water was added
  11. additionmixture was made basic by the addition of 50 percent solution of NaOH until the pH of the solution
  12. filtrationThe white precipitate was filtered off
  13. washwashed with water
  14. dry with materialdried in a vacuum oven at 80° C. to 7.7 grams of tan crystals (melting point 142°-162° C.) which
  15. customwere recrystallized from the minimum amount of a water ethanol mixture
  16. filtrationfiltered off
  17. dry with materialdried in a vacuum oven at 80° C. to 4.8 grams of yellow crystals of 5-[1-(4-methylphenoxy)ethyl]-2-amino-1,3,4-thiadiazole (melting point 178°-180° C.)

Sources & evidence

ORD record
ord-1eab2ed5ed214ce78a6c9af73254d31a
Source dataset
uspto-grants-1981_02
Patent number
US04252961

Reaction notes

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