2-Thiophenesulfonyl chloride → HCID 67109590, compound

HRID 1851353Notes

Reaction equation

HRID 1851353 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[O:11]=[C:8]1[CH2:7][C:6]2[C:10](=[C:2]([NH:1][S:17]([C:13]3[S:12][CH:16]=[CH:15][CH:14]=3)(=[O:19])=[O:18])[CH:3]=[CH:4][CH:5]=2)[NH:9]1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 64233127-aminoindolin-2-one

Product 1

HCID 67109590HCID 67109590, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 7-amino-2-oxo-2,3-dihydro-1H-indole (1.53 g) and pyridine (20 mL) was added thiophene-2-sulfonyl chloride (2.26 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 eluted with ethyl acetate. The eluate was treated with activated carbon and concentrated to give the title compound (2.93 g, yield 97%) as colorless crystals. The crystals were recrystallized from tetrahydrofuran-hexane. melting point>230° 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
  6. washeluted with ethyl acetate
  7. additionThe eluate was treated with activated carbon
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e0925cb090a04d4f95a1e8cc6c2f2973
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…