Thiophenol → 5-Methoxy-3-(phenylthio)benzo[b]thiophene-2-carboxamide

HRID 2226854Notes

Reaction equation

HRID 2226854 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]1[C:10]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:11]=2[S:12][C:13]=1[C:14]([NH2:16])=[O:15].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C=O)C.C(OCC)(=O)C>[CH3:22][O:21][C:19]1[CH:18]=[CH:17][C:11]2[S:12][C:13]([C:14]([NH2:16])=[O:15])=[C:9]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]=2[CH:20]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 106152685-Methoxy-3-(phenylthio)benzo[b]thiophene-2-carboxamideYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Thiophenol (116 μL, 1.13 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (250 mg, 1.03 mmol) in 2 mL of DMF. Diazabicycloundecene (DBU) (169 μL, 1.13 mmol) is added and the mixture is warmed to 80° C. After 2 hours, the reaction mixture is allowed to cool and is diluted with ethyl acetate and washed with 1N NaOH, 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives 5-methoxy-3-(phenylthio)benzo[b]thiophene-2-carboxamide in 84% yield; mp 194°-196° C.

Workup

  1. temperatureto cool
  2. washwashed with 1N NaOH, 1N HCl, water, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-7d6d292c719f47d99e60b0efb8269c41
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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