Phosphorus oxychloride → HCID 3155973, compound

HRID 2287229Notes

Reaction equation

HRID 2287229 reaction equation
[Cl: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>[Cl: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 72862Propanoic acid, 2-(2-chlorophenoxy)-HCID 2723789Thiosemicarbazide

Product 1

HCID 3155973HCID 3155973, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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 10.0 grams (0.050 mole) of 2-(2-chlorophenoxy)propanoic acid, (4.6 grams, 0.050 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 (8.4 grams, 0.055 mole) was slowly added (for 25 minutes) while maintaining the temperature within 85°-90° C. The resulting mixture was refluxed for 75 minutes and stood at ambient temperature for 16 hours. The flask was evacuated by using a water aspirator to remove volatiles (HCl, POCl3 and some dioxane) at 60° C. and then the solution was cooled. 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, washed with water, then dried in a vacuum oven at 80° C. to 9.8 grams of white crystals of 5-[1-(2-chlorophenoxy)ethyl]-2-amino-1,3,4-thiadiazole. (Melting point 160°-164° C.).

Workup

  1. temperaturewhile maintaining the temperature within 85°-90° C
  2. temperatureThe resulting mixture was refluxed for 75 minutes
  3. customThe flask was evacuated
  4. customto remove volatiles (HCl, POCl3
  5. temperaturesome dioxane) at 60° C. and then the solution was cooled
  6. additionFifty (50) milliliters of water was added
  7. addition50 percent solution of NaOH was also added until the pH of the solution
  8. customa solid precipitate formed
  9. filtrationThe solid precipitate was filtered off
  10. washwashed with water
  11. dry with materialdried in a vacuum oven at 80° C. to 9.8 grams of white crystals of 5-[1-(2-chlorophenoxy)ethyl]-2-amino-1,3,4-thiadiazole

Sources & evidence

ORD record
ord-708960bbc251491eadd36477a8d58b44
Source dataset
uspto-grants-1981_05
Patent number
US04269983

Reaction notes

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