Benzene → HCID 25189876, compound

HRID 1517501Notes

Reaction equation

HRID 1517501 reaction equation
[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH2:15])=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2.C1C=CC=CC=1.Cl[S:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)(=[O:25])=[O:24].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH:15][S:23]([C:26]4[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:33][CH:34]=4)(=[O:25])=[O:24])=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2

Participants

7

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 823854-(Chlorosulfonyl)benzoic acidHCID 58420583HCID 58420583, compound

Product 1

HCID 25189876HCID 25189876, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenylamine (0.100 g) was dissolved in pyridine (5 ml) and anhydrous benzene (2 ml), the solution was added with 4-chlorosulfonylbenzoic acid (0.115 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight at room temperature. The reaction mixture was 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 (0.110 g, yield: 57%) as colorless needles (melting point: 215-217° C.).

Workup

  1. extractionmade acidic, and the mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-a35b14332ec742f9a002852f59e4d4a9
Source dataset
uspto-grants-2012_07
Patent number
US08232300B2

Reaction notes

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