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

HRID 128134

反応式

HRID 128134 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7777562742ca4dd4bc933cd89e1f6c06
出典データセット
uspto-grants-1981_03
特許番号
US04257952

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