Ethanol → HCID 57901805, compound

HRID 1851439Notes

Reaction equation

HRID 1851439 reaction equation
[C:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])=[O:14])#[N:2].Cl.[CH2:22]([O:24][C:25](=[O:30])[C@H:26]([CH2:28][SH:29])N)[CH3:23].C(O)C>O>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[S:13]([NH:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[NH:4][C:3]([C:1]1[S:29][CH2:28][CH:26]([C:25]([O:24][CH2:22][CH3:23])=[O:30])[N:2]=1)=[CH:11]2)(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723617Ethyl cysteinate hydrochlorideHCID 57901755HCID 57901755, compound

Product 1

HCID 57901805HCID 57901805, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(2-cyano-1H-indol-7-yl)thiophene-2-sulfonamide (0.30 g), cysteine ethyl ester hydrochloride (0.22 g) and ethanol (10 mL) was heated under reflux overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.11 g, yield 25%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 156-157° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-331e1ea1d3884bf58b687c0fae4c21c5
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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