4-Nitrobenzoic Acid → HCID 86742196, compound

HRID 1253246Notes

Reaction equation

HRID 1253246 reaction equation
[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]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 24386Thionyl ChlorideHCID 13920164Cyclobranol

Product 1

HCID 86742196HCID 86742196, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cfac84752a2d409b9a2a26f77cb5fdee
Source dataset
uspto-grants-1988_05
Patent number
US04748161

Reaction notes

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