Hydrochloric Acid → 3-Chloro-4-iodobenzenesulfonamide

HRID 1694742노트

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HRID 1694742 반응식
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[I:13])N.Cl.[Cl-].[Mg+2].[Cl-].[S:18](=[O:20])=[O:19]>O.C1COCC1.[Cl-].[Na+].O.C(O)(=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([S:18]([NH2:1])(=[O:20])=[O:19])[CH:10]=[CH:11][C:12]=1[I:13]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 2829263-Chloro-4-iodoanilineHCID 5360315Magnesium ChlorideHCID 23668193Sodium Nitrite

생성물 1

HCID 672810493-Chloro-4-iodobenzenesulfonamide

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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온도
34 °C

실험 절차

A solution of sodium nitrite (3.27 g) in water was added dropwise over 1 h to a stirred solution of 3-chloro-4-iodoaniline (10.0 g) in a mixture of THF (120 ml) and concentrated hydrochloric acid (50 ml) at −5 to −1° C. Magnesium chloride (6.39 g) was then added and the resulting mixture poured into a stirred solution of acetic acid (50 ml) saturated with sulfur dioxide and containing cuprous chloride (2.14 g). After heating at 34° C. for 30 min, the mixture was poured into brine, extracted with EtOAc, washed with aqueous sodium bicarbonate and brine, dried (MgSO4) and evaporated. The residue was dissolved in THF (100 ml), 0.880 ammonia (100 ml) added and stirred for 2 h. The mixture was diluted with brine, extracted with EtOAc, washed with brine, dried (MgSO4) and evaporated. The residue was treated with isohexane/ether (4:1) and filtered to give the subtitle compound. Yield 5.67 g.

후처리

  1. extractionextracted with EtOAc
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in THF (100 ml)
  6. addition0.880 ammonia (100 ml) added
  7. additionThe mixture was diluted with brine
  8. extractionextracted with EtOAc
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. additionThe residue was treated with isohexane/ether (4:1)
  13. filtrationfiltered

출처 및 근거

ORD 기록
ord-cce7a7a4ebbd4f47837e644b16258573
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158820B2

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