Acetic Acid → methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

HRID 581655

반응식

HRID 581655 반응식
[C:1]([NH:5][S:6]([C:9]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.Cl>[Fe].O>[NH2:19][C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([S:6](=[O:8])(=[O:7])[NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH:18]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15240542methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate

생성물 1

HCID 10946074methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate수율 83.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

50.0 g (0.158 mol) of methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate (prepared in accordance with DE-OS 4 236 902) are added to a mixture of 180 ml of acetic acid and 75 ml of water and the mixture is heated to 80° C. 26.5 g (0.474 mol) of iron powder are added in portions such that the temperature does not rise above 85° C. The mixture is then stirred at 80° C. for 4 hours, 85 ml of 2N HCl are added at this temperature and the mixture is allowed to cool to 25° C. The solid is filtered off and washed thoroughly with water. It is then extracted hot 3 times with 250 ml of ethyl acetate each time. The ethyl acetate phase is evaporated and the residue is triturated with diisopropyl ether and dried. 37.7 g (83% of theory) of methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate of melting point 198-199° C. are obtained.

후처리

  1. customdoes not rise above 85° C
  2. temperatureto cool to 25° C
  3. filtrationThe solid is filtered off
  4. washwashed thoroughly with water
  5. extractionIt is then extracted hot 3 times with 250 ml of ethyl acetate each time
  6. customThe ethyl acetate phase is evaporated
  7. customthe residue is triturated with diisopropyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-c3a8ecc33de4441cb44045ddec8c755a
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922645

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