2-Propanesulfonyl chloride → HCID 57901618, compound

HRID 1851438Notes

Reaction equation

HRID 1851438 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11](=[O:15])[CH2:10][CH2:9][CH2:8][C:7]2=1.[CH3:16][CH:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18]>N1C=CC=CC=1>[O:15]=[C:11]1[C:12]2[NH:13][C:14]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[NH:1][S:19]([CH:17]([CH3:18])[CH3:16])(=[O:21])=[O:20])[C:7]=2[CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 57901659HCID 57901659, compound

Product 1

HCID 57901618HCID 57901618, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 8-amino-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.35 g) and pyridine (8 mL) was added propane-2-sulfonyl chloride (0.24 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.94 g, yield 19%) was obtained as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate. melting point 267-268° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10% aqueous citric acid solution was added
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9c693e765e464c058f63f2b4b6da1d93
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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