Sodium methanethiolate → 5-Methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamide

HRID 2226853Notes

Reaction equation

HRID 2226853 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:6]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:7]=2[S:8][C:9]=1[C:10]([NH2:12])=[O:11]>CN(C=O)C.C(OCC)(=O)C>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:7]2[S:8][C:9]([C:10]([NH2:12])=[O:11])=[C:5]([S:2][CH3:1])[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamide

Product 1

HCID 108247755-Methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamideYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium thiomethoxide (93 mg, 1.32 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. After 1 hour, an additional amount of sodium thiomethoxide (13 mg) is added. The reaction mixture 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-(methylthio)benzo[b]thiophene-2-carboxamide in 72% yield; mp=171°-173° C.

Workup

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

Sources & evidence

ORD record
ord-ba72a96911714921855ee1f0c6826876
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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