2-Thiophenesulfonyl chloride → HCID 57901829, compound

HRID 1851434Notes

Reaction equation

HRID 1851434 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.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[S:21](Cl)(=[O:23])=[O:22]>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:21]([C:17]3[S:16][CH:20]=[CH:19][CH:18]=3)(=[O:23])=[O:22])[C:7]=2[CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57901659HCID 57901659, compound

Product 1

HCID 57901829HCID 57901829, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 8-amino-2,3,4,9-tetrahydro-1H-carbazol-1-one (1.20 g) and pyridine (20 mL) was added thiophene-2-sulfonyl chloride (1.30 g) 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 86%) was obtained as colorless crystals from a fraction eluted with tetrahydrofuran. The crystals were recrystallized from tetrahydrofuran-hexane. melting point>280° 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-5716d06fb5d446778cfc8d1c953626cb
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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