Acetic Acid → 6-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide hydrochloride

HRID 2164541

반응식

HRID 2164541 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:19])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:8]2=O)=[CH:4][C:3]=1[S:20]([NH2:23])(=[O:22])=[O:21].O=C1C2C(=CC=CC=2)C(=O)N1.C(O)(=O)C.Cl>CN(C)C=O.[Zn].C(O)(=O)C.[Zn]>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:19])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:8]2)=[CH:4][C:3]=1[S:20]([NH2:23])(=[O:22])=[O:21]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6809Phthalimide2회HCID 134731836-Chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide

생성물 1

HCID 204048526-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide hydrochloride

시약·촉매·용매 3

HCID 23994Zinc촉매2회HCID 57475673ZINC acetic acid촉매HCID 6228Dimethylformamide용매

실험 절차

Zinc-acetic acid reduction of 6-chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide. Zinc dust (0.5 mole) is added in one portion to the 1,3-dioxoisoindole (0.1 mole) of part (a) in 800 ml. of acetic acid. The reaction mixture is stirred at room temperature for 1.0 hr. and then heated to reflux for a 6 hr. period during which time additional 9.0 g. portions of zinc are added at the end of 3, 4, and 5 hr., respectively. After stirring overnight, the reaction mixture is filtered and the filtrate concentrated to dryness under reduced pressure with additional water added to the residue and removed in vacuo to remove traces of acetic acid. Residual material is slurried in water, filtered, and the filtrate concentrated to dryness. Residual material is stirred with saturated sodium bicarbonate solution and an immiscible organic solvent such as hot ethyl acetate. The organic fraction is separated, dried over MgSO4 and concentrated to provide the product as the free base. The free base taken up in dimethylformamide and acidified with ethanolic hydrogen chloride affords 6-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide hydrochloride.

후처리

  1. temperatureand then heated
  2. temperatureto reflux for a 6 hr
  3. stirringAfter stirring overnight
  4. filtrationthe reaction mixture is filtered
  5. concentrationthe filtrate concentrated to dryness under reduced pressure with additional water
  6. additionadded to the residue
  7. customremoved in vacuo
  8. customto remove traces of acetic acid
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated to dryness
  11. stirringResidual material is stirred with saturated sodium bicarbonate solution
  12. customThe organic fraction is separated
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated
  15. customto provide the product as the free base

출처 및 근거

ORD 기록
ord-9415240d1fc74991ab09c1626e1fa663
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04505911

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