Succinic anhydride → 4-(4-(Methylsulfonamido)phenyl)-4-oxobutanoic acid

HRID 466347

반응식

HRID 466347 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][S:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])=[O:7].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1>C(=S)=S>[CH3:5][S:6]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:15]=1)(=[O:8])=[O:7]

참가 물질

5

반응물 3

HCID 7922Succinic anhydrideHCID 70970Methanesulfonamide, N-phenyl-HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 113692744-(4-(Methylsulfonamido)phenyl)-4-oxobutanoic acid

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

A mechanically stirred suspension of aluminum chloride (88.0 g, 0.66 moles) and 150 ml of carbon disulfide under N2 is cooled in an ice bath. Methanesulfonanilide as prepared in Preparation 1 (30.0 g, 0.175 mol) and succinic anhydride (17.5 g, 0.175 mol) are combined and added rapidly to the cooled reaction mixture. The ice bath is removed and the mixture is stirred at ambient temperature for 6 hours. The reaction mixture is then heated to 55° C. and allowed to continue for 18 hours. The reaction mixture is separated into two layers the bottom of which solidifies. The upper layer is decanted and the remaining solid layer is decomposed with ice. The resulting suspension is filtered and the solid is washed several times with methylene chloride and dissolved in a mixture of saturated sodium bicarbonate (500 ml) and water (500 ml). This solution is acidified (pH2) with HCl and the resulting precipitate is collected by filtration, redissolved in NaHCO3 and reprecipitated with HCl. The solid, 4-[(methylsulfonyl)amino]-γ-oxobenzenebutanoic acid, is collected by filtration and dried to give the title compound with mp 198°-200° C.

후처리

  1. temperatureis cooled in an ice bath
  2. additionadded rapidly to the cooled reaction mixture
  3. customThe ice bath is removed
  4. temperatureThe reaction mixture is then heated to 55° C.
  5. waitto continue for 18 hours
  6. customThe reaction mixture is separated into two layers the bottom of which
  7. customThe upper layer is decanted
  8. filtrationThe resulting suspension is filtered
  9. washthe solid is washed several times with methylene chloride
  10. dissolutiondissolved in a mixture of saturated sodium bicarbonate (500 ml) and water (500 ml)
  11. filtrationthe resulting precipitate is collected by filtration
  12. dissolutionredissolved in NaHCO3
  13. customreprecipitated with HCl
  14. filtrationThe solid, 4-[(methylsulfonyl)amino]-γ-oxobenzenebutanoic acid, is collected by filtration
  15. customdried

출처 및 근거

ORD 기록
ord-08a036ed070e46b3ab416ad169413b3e
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155268

연결된 노트

불러오는 중…