2-(4-Chlorophenoxy)propionic acid → 5-[1-(4-Chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-amine

HRID 444368노트

반응식

HRID 444368 반응식
[Cl: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>[Cl: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

참가 물질

5

반응물 3

HCID 187032-(4-Chlorophenoxy)propionic acidHCID 24813Phosphorus oxychloride2회HCID 2723789Thiosemicarbazide

생성물 1

HCID 31559725-[1-(4-Chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-amine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Into a 100 milliliter, 3-neck flask adapted with a Claisen adaptor, paddle stirrer, thermometer, an addition funnel and condensor, was charged with 10.0 grams (0.050 mole) of 2-(4-chlorophenoxy)propanoic acid, (4.6 grams, 0.050 mole) of thiosemicarbazide and 30 ml. of dioxane. The slurry was heated to 90 degrees centigrade and the addition funnel was charged with phosphorous oxychloride (POCl3). The POCl3 (8.4 gram, 0.055 mole) was slowly added (for 30 minutes) while maintaining the temperature within 85-90 degrees centigrade. 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 sixty degrees centigrade 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 70 degrees centigrade to white crystals which were recrystallized from the minimum amount of H2O/ethanol mixture, filtered and then dried in a vacuum oven at 80 degrees centigrade to white crystals of 5-[1-(4-chlorophenoxy) ethyl]-2-amino-1,3,4-thiadiazole. (Melting point 162-166 degrees centigrade).

후처리

  1. temperatureThe slurry was heated to 90 degrees centigrade
  2. temperaturewhile maintaining the temperature within 85-90 degrees centigrade
  3. temperatureThe resulting mixture was refluxed for 75 minutes
  4. customThe flask was evacuated
  5. customto remove volatiles (HCl, POCl3
  6. temperaturesome dioxane) at sixty degrees centigrade and then the solution was cooled
  7. additionFifty (50) milliliters of water was added
  8. addition50 percent solution of NaOH was also added until the pH of the solution
  9. customa solid precipitate formed
  10. filtrationThe solid precipitate was filtered off
  11. washwashed with water
  12. customdried in a vacuum oven at 70 degrees centigrade to white crystals which
  13. customwere recrystallized from the minimum amount of H2O/ethanol mixture
  14. filtrationfiltered
  15. dry with materialdried in a vacuum oven at 80 degrees centigrade to white crystals of 5-[1-(4-chlorophenoxy) ethyl]-2-amino-1,3,4-thiadiazole

출처 및 근거

ORD 기록
ord-02b55dd0bb584fe69ec6690ccfabb02a
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04264353

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