2-Thiophenesulfonyl chloride → HCID 57901831, compound

HRID 1851441Notes

Reaction equation

HRID 1851441 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11](=[O:14])[CH2:12][CH3:13])=[C:7]2[CH3:15].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:15][C:7]1[C:6]2[C:10](=[C:2]([NH:1][S:21]([C:17]3[S:16][CH:20]=[CH:19][CH:18]=3)(=[O:23])=[O:22])[CH:3]=[CH:4][CH:5]=2)[NH:9][C:8]=1[C:11](=[O:14])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57901870HCID 57901870, compound

Product 1

HCID 57901831HCID 57901831, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1-(7-amino-3-methyl-1H-indol-2-yl)propan-1-one (0.17 g) and pyridine (6 mL) was added thiophene-2-sulfonyl chloride (0.18 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 (0.19 g, yield 65%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point >185° 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-e73d68f4487747178a8a5c82fa97f52f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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