Thioacetamide → HCID 10847601, compound

HRID 2226859Notes

Reaction equation

HRID 2226859 reaction equation
C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.Cl[C:24]1[C:25]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:26]=2[S:27][C:28]=1[C:29]([NH2:31])=[O:30].C(N)(=[S:40])C>CN(C=O)C.C(OCC)(=O)C>[SH:40][C:24]1[C:25]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:26]=2[S:27][C:28]=1[C:29]([NH2:31])=[O:30]

Participants

6

Reactant 3

HCID 2723949ThioacetamideHCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 10847601HCID 10847601, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Diazabicycloundecene (DBU) (1.8 mL, 12.3 mmol) is added to a room temperature solution of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (1.0 g, 4.1 mmol) and thioacetamide (1.0 g, 13.1 mmol) in 10 mL of DMF. The mixture is warmed to 80° C. for 5.5 hours. The reaction mixture is allowed to cool and is diluted with ethyl acetate and washed with 1N HCl and water. The organic layer is extracted four times with 1N NaOH followed by water. The basic layers are combined and acidified with 6N HCl. The precipitate is filtered and washed with water. Recrystallization from ethyl acetate:hexane gives 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide in 71% yield; mp=205° C. dec.

Workup

  1. temperatureto cool
  2. washwashed with 1N HCl and water
  3. extractionThe organic layer is extracted four times with 1N NaOH
  4. filtrationThe precipitate is filtered
  5. washwashed with water
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a618b09764984e3482a24f5621defd72
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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