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

HRID 2164540

反応式

HRID 2164540 の反応式
[Sn].Cl.[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:21])[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:10]2=O)=[CH:6][C:5]=1[S:22]([NH2:25])(=[O:24])=[O:23].O=C1C2C(=CC=CC=2)C(=O)N1.Cl.[Sn]>CO>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:21])[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:10]2)=[CH:6][C:5]=1[S:22]([NH2:25])(=[O:24])=[O:23]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6809PhthalimideHCID 5352426Tin atom2 回HCID 134731836-Chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamideHCID 86739978Tin hydrochloride

生成物 1

HCID 134731936-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Tin-Hydrochloric Acid Reduction of 6-Chloro-2,3-dihydro-1,3-dioxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide. A mixture of the above part (a) 1,3-dioxoisoindole (18 g., 0.051 mole), 120 ml. of methanol and 60 ml. of concentrated hydrochloric acid was heated with 30 mesh granulated tin metal added as indicated: 15 g. at 65°-70° for 6 hr., then 8 g. at 60°-65° for 16 hr. and finally 6 g. at 70°-75° for a 7 hr. period. The reaction mixture is cooled, filtered and concentrated to about 60 ml. volume. Addition of about 60 ml. of methanol to the concentrated mixture provided on standing 10 g., of a tin salt complex. This material was further purified by stirring with 1 liter of 50% methanol and 20 ml. of 1N hydrochloric acid while slowly introducing a gaseous stream of hydrogen sulfide (H2S) during a 1 hr. period at 45°-50°. The mixture is stirred at 40°-45° for 16 hr. and then concentrated slightly to remove excess H2S. Activated charcoal was added and the mixture filtered. Concentration of the filtrate to about 50 ml. and dilution with 1 ml. of 6N hydrochloric acid and cooling yielded 2.2 g. (12%) of white solid. Crystallization from aqueous methanol afforded analytically pure 6-chloro-2,3-dihydro-3-oxo-2-(2-pyridinylmethyl)-1H-isoindole-5-sulfonamide as the hydrochloride salt, m.p. 264°-266°.

後処理

  1. additionadded
  2. waitat 60°-65° for 16 hr
  3. waitat 70°-75° for a 7 hr
  4. temperatureThe reaction mixture is cooled
  5. filtrationfiltered
  6. concentrationconcentrated to about 60 ml
  7. additionAddition of about 60 ml
  8. customof methanol to the concentrated mixture provided
  9. customThis material was further purified
  10. additionof 1N hydrochloric acid while slowly introducing a gaseous stream of hydrogen sulfide (H2S) during a 1 hr
  11. customat 45°-50°
  12. stirringThe mixture is stirred at 40°-45° for 16 hr
  13. concentrationand then concentrated slightly
  14. customto remove excess H2S
  15. additionActivated charcoal was added
  16. filtrationthe mixture filtered
  17. temperatureof 6N hydrochloric acid and cooling
  18. customyielded 2.2 g
  19. customCrystallization from aqueous methanol

出典と根拠

ORDレコード
ord-48640b94e2a648eb95238ed931515ef5
出典データセット
uspto-grants-1985_03
特許番号
US04505911

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