2-(3,4-Dichlorophenoxy)propanoic acid → HCID 12880030, compound

HRID 2287037Notes

Reaction equation

HRID 2287037 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:5][CH:6]([CH3:10])[C:7](O)=O.[NH2:15][NH:16][C:17]([NH2:19])=[S:18].O1CCOCC1.P(Cl)(Cl)(Cl)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:5][CH:6]([C:7]1[S:18][C:17]([NH2:19])=[N:16][N:15]=1)[CH3:10]

Participants

6

Reactant 4

HCID 187042-(3,4-Dichlorophenoxy)propanoic acidHCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 2723789Thiosemicarbazide

Product 1

HCID 12880030HCID 12880030, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 100 milliliter, 3-neck flask adapted with a Claisen adaptor, paddle stirrer, thermometer, an addition funnel and condenser, was charged with 9.4 grams (0.040 mole) of 2-(3,4-dichlorophenoxy)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, 0.044 mole) which was slowly added (for 15 minutes) while maintaining the temperature within 85°-90° C. The resulting mixture was refluxed for approximately 100 minutes, and then topped with a water aspirator to remove volatiles (HCl, POCl3 and some dioxane). Fifty (50) milliliters of water was added and 50 percent solution of NaOH was also added until the pH of the solution was 10; a solid precipitate formed. The solid precipitate was filtered off and partially air dried, and was recrystallized from the minimum amount of H2O/ethanol mixture, filtered and then dried in a vacuum oven at 80° C. to 8.0 grams of fluffy white crystals of 5-[1-(3,4-dichlorophenoxy)ethyl]-2amino-1,3,4-thiadiazole. (Melting point 136°-138° C.).

Workup

  1. additionwas slowly added (for 15 minutes)
  2. temperaturewhile maintaining the temperature within 85°-90° C
  3. temperatureThe resulting mixture was refluxed for approximately 100 minutes
  4. customto remove volatiles (HCl, POCl3
  5. additionFifty (50) milliliters of water was added
  6. addition50 percent solution of NaOH was also added until the pH of the solution
  7. customa solid precipitate formed
  8. filtrationThe solid precipitate was filtered off
  9. custompartially air dried
  10. customwas recrystallized from the minimum amount of H2O/ethanol mixture
  11. filtrationfiltered
  12. dry with materialdried in a vacuum oven at 80° C. to 8.0 grams of fluffy white crystals of 5-[1-(3,4-dichlorophenoxy)ethyl]-2amino-1,3,4-thiadiazole

Sources & evidence

ORD record
ord-7a49ddde871f4e00a80618b025a6caa0
Source dataset
uspto-grants-1981_05
Patent number
US04268675

Reaction notes

Loading…