4-Nitrobenzoic Acid → HCID 86742196、化合物

HRID 1253246ノート

反応式

HRID 1253246 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:17][C@@H:18]([C@@H:26]1[C@@:30]2([CH3:47])[CH2:31][CH2:32][C@@:33]34[CH2:39][C@:38]53[CH2:40][CH2:41][C@H:42]([OH:46])[C:43]([CH3:45])([CH3:44])[C@@H:37]5[CH2:36][CH2:35][C@H:34]4[C@:29]2([CH3:48])[CH2:28][CH2:27]1)[CH2:19][CH2:20][C:21]([CH3:25])=[C:22]([CH3:24])[CH3:23]>O1CCOCC1>[CH3:17][C@@H:18]([C@@H:26]1[C@@:30]2([CH3:47])[CH2:31][CH2:32][C@@:33]34[CH2:39][C@:38]53[CH2:40][CH2:41][C@H:42]([OH:46])[C:43]([CH3:45])([CH3:44])[C@@H:37]5[CH2:36][CH2:35][C@H:34]4[C@:29]2([CH3:48])[CH2:28][CH2:27]1)[CH2:19][CH2:20][C:21]([CH3:25])=[C:22]([CH3:23])[CH3:24].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O-:10])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 61084-Nitrobenzoic AcidHCID 24386Thionyl ChlorideHCID 13920164Cyclobranol

生成物 1

HCID 86742196HCID 86742196、化合物収率 90%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

To p-nitrobenzoic acid (1 g, 0.006 mole) dissolved in dioxane (20 ml) was added thionyl chloride (3 ml, 7 equivalents) and the mixture was stirred at 60° C. for 2 hours. The resulting mixture was evaporated under reduced pressure, then dioxane (20 ml) and pyridine (3 ml) were added to the resulting residue. Cyclobranol (2 g, 0.0045 mole) was added to the solution and the mixture was stirred at 60° C. for 2 hours to complete the reaction. The mixture was evaporated under reduced pressure, and the residue was extracted with chloroform (30 ml). The extract was washed successively with 3% aqueous sodium carbonate, water, and saturated brine, dried, and evaporated to dryness under reduced pressure. The crude crystals were washed with ethanol (50 ml), and recrystallized from ethyl acetate, giving cyclobranol-p-nitrobenzoate (2.28 g) in a 90% yield. m.p. 244°-245° C.

後処理

  1. customThe resulting mixture was evaporated under reduced pressure
  2. additiondioxane (20 ml) and pyridine (3 ml) were added to the resulting residue
  3. stirringthe mixture was stirred at 60° C. for 2 hours
  4. customthe reaction
  5. customThe mixture was evaporated under reduced pressure
  6. extractionthe residue was extracted with chloroform (30 ml)
  7. washThe extract was washed successively with 3% aqueous sodium carbonate, water, and saturated brine
  8. customdried
  9. customevaporated to dryness under reduced pressure
  10. washThe crude crystals were washed with ethanol (50 ml)
  11. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-cfac84752a2d409b9a2a26f77cb5fdee
出典データセット
uspto-grants-1988_05
特許番号
US04748161

反応ノート

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