Iodine → Ethyl 4,6-dichloro-3-iodo-1H-indole-2-carboxylate

HRID 440378노트

반응식

HRID 440378 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2.[OH-].[Na+].[I:19]I>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[C:4]([I:19])=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2

참가 물질

6

반응물 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 2736407ethyl 4,6-dichloro-1H-indole-2-carboxylate

생성물 1

HCID 15814285Ethyl 4,6-dichloro-3-iodo-1H-indole-2-carboxylate

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8857Ethyl Acetate용매

실험 절차

Combine 4,6-dichloro-indole-2-carboxylic acid, ethyl ester (5.2 g, 20.0 mmol) and sodium hydroxide (0.80 g, 20 mmol) in ethanol (250 mL). Add iodine (5.1 g, 20.0 mmol) as a solution in ethanol (100 mL). After 1 hour, concentrate the reaction mixture in vacuo to obtain a residue. Dissolve the residue in ethyl acetate and extract with 1M hydrochloric acid solution and then with saturated sodium chloride solution. Dry the organic layer over magnesium sulfate and evaporate in vacuo. Chromatograph on silica gel eluting with 25% ethyl acetate/hexane. Combine the product containing fractions and evaporate in vacuo. Recrystallize form ethyl acetate/hexane to give the title compound as a solid; mp: 218°-220° C. Elem. Anal. calculated for C11H8Cl2INO2 : C, 34.41; H, 2.10; N, 3.65. Found: C, 34.67; H, 2.09; N, 3.68.

후처리

  1. concentrationconcentrate the reaction mixture in vacuo
  2. customto obtain a residue
  3. extractionextract with 1M hydrochloric acid solution
  4. dry with materialDry the organic layer over magnesium sulfate
  5. customevaporate in vacuo
  6. additioncontaining fractions
  7. customevaporate in vacuo
  8. customRecrystallize
  9. customform ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-cb1baf95815e4de4b675ba97fe9fa680
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519048

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