Methanesulfonic Acid → 3-(Isobutylamino)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole 3-(Acetamido)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole

HRID 128134

Reaktionsgleichung

Reaktionsgleichung von HRID 128134
[C:1](NC1CCC(=O)CC1)(=O)C.Cl.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21]N.CS(O)(=O)=O.[C:28]([NH:31][CH:32]1[CH2:44][C:43]2[C:42]3[C:37](=[C:38]([F:46])[CH:39]=[C:40]([F:45])[CH:41]=3)[NH:36][C:35]=2[CH2:34][CH2:33]1)(=[O:30])[CH3:29]>C(O)C>[C:28]([NH:31][CH:32]1[CH2:44][C:43]2[C:42]3[C:37](=[C:38]([F:46])[CH:39]=[C:40]([F:45])[CH:41]=3)[NH:36][C:35]=2[CH2:34][CH2:33]1)(=[O:30])[CH3:29].[CH2:35]([NH:36][CH:37]1[CH2:38][C:39]2[C:16]3[C:15](=[C:14]([F:13])[CH:19]=[C:18]([F:20])[CH:17]=3)[NH:21][C:40]=2[CH2:41][CH2:42]1)[CH:43]([CH3:44])[CH3:1]

Komponenten

6

Edukt 4

HCID 6395Methanesulfonic AcidHCID 538565N-(4-Oxocyclohexyl)acetamideHCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 128918073-(Acetamido)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole

Produkt 1

HCID 234705183-(Isobutylamino)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole 3-(Acetamido)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 15.5 g. of 4-acetamidocyclohexanone, 18 g. of 2,4-difluorophenylhydrazine hydrochloride and 10 g. of methanesulfonic acid in 200 ml. of absolute ethyl alcohol was heated under reflux for two hours, cooled, filtered, and the filtrate was evaporated to dryness under reduced pressure. The residual oil was triturated with water and the resulting solid was collected by filtration, triturated with ether, and recrystallized by dissolving in methanol, adding toluene, and evaporating the methanol to give 8.5 g. of 3-(acetamido)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole, m.p. 179°-183° C.

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customThe residual oil was triturated with water
  6. filtrationthe resulting solid was collected by filtration
  7. customtriturated with ether
  8. customrecrystallized
  9. dissolutionby dissolving in methanol
  10. additionadding toluene
  11. customevaporating the methanol
  12. customto give 8.5 g

Quellen und Nachweise

ORD-Eintrag
ord-7777562742ca4dd4bc933cd89e1f6c06
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04257952

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