Benzene → 4-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)sulfamoyl]benzoic acid

HRID 1517493Notes

Reaction equation

HRID 1517493 reaction equation
[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH2:14].C1C=CC=CC=1.Cl[S:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1)(=[O:24])=[O:23].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH:14][S:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:32][CH:33]=1)(=[O:24])=[O:23]

Participants

7

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 823854-(Chlorosulfonyl)benzoic acidHCID 58420580HCID 58420580, compound

Product 1

HCID 673911474-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)sulfamoyl]benzoic acidYield 75.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

5,6,6a,7,8,9-Hexahydro-4H-2-phenalenylamine (0.130 g) was dissolved in pyridine (5 ml) and anhydrous benzene (2 ml), the solution was added with 4-chlorosulfonylbenzoic acid (0.161 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight at room temperature. The reaction mixture was made to be at 60° C., stirred for 3 hours, left to cool, then added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethyl acetate-n-hexane to obtain the title compound (0.194 g, yield: 75%) as brown needles (melting point: 266-268° C.).

Workup

  1. customto be at 60° C.
  2. stirringstirred for 3 hours
  3. waitleft
  4. temperatureto cool
  5. extractionmade acidic, and the mixture was extracted with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customthe resulting residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-e47344bdb40146ae8c4c978453ba329e
Source dataset
uspto-grants-2012_07
Patent number
US08232300B2

Reaction notes

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