2-Thiophenesulfonyl chloride → HCID 136060832, compound

HRID 1851509Notes

Reaction equation

HRID 1851509 reaction equation
[S:1]1[C:5]([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][C:9]=3[NH2:15])=[N:4][CH:3]=[N: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>[S:1]1[C:5]([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][C:9]=3[NH:15][S:21]([C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)(=[O:23])=[O:22])=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 136060813HCID 136060813, compound

Product 1

HCID 136060832HCID 136060832, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-(1,2,4-thiadiazol-5-yl)-1H-indole-7-amine (0.35 g) and pyridine (8 ml) was added thiophene-2-sulfonyl chloride (0.34 g) at 0° C., and the mixture was stirred at room temperature overnight. 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 (0.25 g, yield 43%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point 232-233° 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
  6. washeluted with ethyl acetate
  7. additionThe eluate was treated with activated carbon
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7ec6bf648c654ecaa2e075311232e4e1
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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