Phosphorus oxychloride → HCID 23460870, compound

HRID 2287034Notes

Reaction equation

HRID 2287034 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[O:5][CH:6]([CH3:10])[C:7](O)=O.[NH2:15][NH:16][C:17]([NH2:19])=[S:18].P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[O:5][CH:6]([C:7]1[S:18][C:17]([NH2:19])=[N:16][N:15]=1)[CH3:10]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 2723789ThiosemicarbazideHCID 200597612-(3,5-Dichlorophenoxy)propanoic acid

Product 1

HCID 23460870HCID 23460870, 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 9.4 grams (0.040 mole) of 2-(3,5-dichlorophenoxy)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 22 minutes) while maintaining the temperature within 85°-90° C. The resulting mixture was refluxed for 60 minutes. The flask was evacuated by using 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; an oil formed. The oil was extracted with diethylether, dried over MgSO4, filtered, and topped in a roto-vac at 70° C. to yield 7.9 grams of a pale yellow oil of 5-[1-(3,5-dichlorophenoxy)ethyl]-2-amino-1,3,4-thiadiazol.

Workup

  1. temperaturewhile maintaining the temperature within 85°-90° C
  2. temperatureThe resulting mixture was refluxed for 60 minutes
  3. customThe flask was evacuated
  4. customto remove volatiles (HCl, POCl3
  5. additionsome dioxane), fifty (50) milliliters of water was added
  6. addition50 percent solution of NaOH was also added until the pH of the solution
  7. customan oil formed
  8. extractionThe oil was extracted with diethylether
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customtopped in a roto-vac at 70° C.

Sources & evidence

ORD record
ord-c7b5211e5a02428c9015a84f4b594daa
Source dataset
uspto-grants-1981_05
Patent number
US04268675

Reaction notes

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