Phosphorus oxychloride → HCID 17604532, compound

HRID 1856096Notes

Reaction equation

HRID 1856096 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6](O)=O.[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][CH:11]=[CH:10][C:3]=1[O:4][CH:5]([C:6]1[S:17][C:16]([NH2:18])=[N:15][N:14]=1)[CH3:9]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 1655922-(2-METHYLPHENOXY)PROPANOIC ACIDHCID 2723789Thiosemicarbazide

Product 1

HCID 17604532HCID 17604532, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A 100 milliliter flask adapted with a paddle stirrer, thermometer, an addition funnel, condenser and drying tube was charged with 7.2 grams (0.040 mole) of 2-(2-methylphenoxy)propanoic acid, 3.6 grams, (0.040 mole) of thiosemicarbazide and 30 milliliters of dioxane. The slurry was heated to 90° C. and the addition funnel was charged with phosphorous oxychloride (POCl3). The POCl3 (6.7 grams; 0.044 mole) was slowly added (for 20 minutes) while maintaining the temperature within 90°-95° C., a gooey white precipitate formed. 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 precipate was filtered off, washed with water and dissolved in the minimum amount of 95 percent ethanol, to which a small amount of a 10 percent sodium hydroxide solution was added to make the ethanol solution basic. Water was added until a precipitate formed and the solution was cooled in the refrigerator, then suctioned filtered. The precipitate was washed with water, and dried in a vacuum oven at 70° C. to white crystals of 5-[1-(2-methylphenoxy)ethyl]-2-amino-1,3,4-thiadiazole (6.8 grams--melting point 176°-179° C.)

Workup

  1. customA 100 milliliter flask adapted with a paddle stirrer
  2. customthermometer, an addition funnel, condenser and drying tube
  3. temperaturewhile maintaining the temperature within 90°-95° C.
  4. customa gooey white precipitate formed
  5. additionWhen the addition
  6. temperaturewas refluxed for 60 minutes
  7. customThe flask was evacuated
  8. customto remove volatiles (HCl, POCl3
  9. additionsome dioxane), and then 50 milliliters of water was added
  10. additionmixture was made basic by the addition of 50 percent solution of NaOH until the pH of the solution
  11. filtrationThe white precipate was filtered off
  12. washwashed with water
  13. dissolutiondissolved in the minimum amount of 95 percent ethanol, to which a small amount of a 10 percent sodium hydroxide solution
  14. additionwas added
  15. additionWater was added until a precipitate
  16. customformed
  17. temperaturethe solution was cooled in the refrigerator
  18. filtrationsuctioned filtered
  19. washThe precipitate was washed with water
  20. dry with materialdried in a vacuum oven at 70° C. to white crystals of 5-[1-(2-methylphenoxy)ethyl]-2-amino-1,3,4-thiadiazole (6.8 grams--melting point 176°-179° C.)

Sources & evidence

ORD record
ord-c5ccec4ff8eb48fdbca2b9a58fbf6a99
Source dataset
uspto-grants-1980_08
Patent number
US04218236

Reaction notes

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