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

HRID 2164541

反応式

HRID 2164541 の反応式
[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]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6809Phthalimide2 回HCID 134731836-Chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒2 回HCID 57475673ZINC acetic acid触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9415240d1fc74991ab09c1626e1fa663
出典データセット
uspto-grants-1985_03
特許番号
US04505911

関連ノート

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