Acetohydrazide → 5-(p-Chlorophenyl)-2-furoic Acid 1-Acetylhydrazine

HRID 236270

반응식

HRID 236270 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:16]([NH:19][NH2:20])(=[O:18])[CH3:17]>S(Cl)(Cl)=O.C(Cl)(Cl)Cl>[C:16]([NH:19][NH2:20])(=[O:18])[CH3:17].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 14039AcetohydrazideHCID 7266935-(4-Chlorophenyl)-2-furoic acid

생성물 1

HCID 704339805-(p-Chlorophenyl)-2-furoic Acid 1-Acetylhydrazine수율 64%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 24386Thionyl Chloride용매

실험 절차

A mixture of 111.5 g (0.50 mole) of 5-(p-chlorophenyl)-2-furoic acid in 500 ml of thionyl chloride was heated at refluxed for 13/4 hr. After slight cooling, the reaction mixture was filtered and the filtrate was concentrated in a water bath at reduced pressure to a creamy solid. The solid was dissolved in 400 ml of chloroform. To this chloroform solution under stirring at room temperature was added a suspension of 74 g (1.0 mole) of acetylhydrazine in 900 ml of chloroform. Addition was completed in about 20 min. White creamy solid separated fairly readily while the temperature rose to about 45°. The mixture was allowed to stir at ambient temperature overnight. The mixture was filtered and the solid was washed with chloroform and air dried. The solid was further triturated with water, filtered, washed with water again and air dried. The yield of crude product was 120 g (89%). Recrystallization from ethyl acetate gave 95 g of product, m.p. 206°-208°.

후처리

  1. temperaturewas heated
  2. temperatureat refluxed for 13/4 hr
  3. filtrationAfter slight cooling, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in a water bath at reduced pressure to a creamy solid
  5. dissolutionThe solid was dissolved in 400 ml of chloroform
  6. additionwas added
  7. additionAddition
  8. customWhite creamy solid separated fairly readily while the temperature
  9. customrose to about 45°
  10. stirringto stir at ambient temperature overnight
  11. filtrationThe mixture was filtered
  12. washthe solid was washed with chloroform and air
  13. customdried
  14. customThe solid was further triturated with water
  15. filtrationfiltered
  16. washwashed with water again
  17. customair dried
  18. customRecrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-734103e3ef174dbd913d36031004da25
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04643996

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