o-Toluenesulfonyl chloride → HCID 57901858, compound

HRID 1851437Notes

Reaction equation

HRID 1851437 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][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH: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)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 57901659HCID 57901659, compound

Product 1

HCID 57901858HCID 57901858, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 8-amino-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.30 g) and pyridine (8 mL) was added 2-methylbenzenesulfonyl chloride (0.26 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 (0.38 g, yield 73%) was obtained as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 255-256° C. (decomposition).

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-2a24869537f84b63a673548604ec2c4c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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