2-Mercaptoacetamide → 3-Amino-7-bromobenzo[b]thiophene-2-carboxamide

HRID 2054916Notes

Reaction equation

HRID 2054916 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[SH:11][CH2:12][C:13]([NH2:15])=[O:14].C[O-].[Na+]>CN(C=O)C.CO>[NH2:6][C:5]1[C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[C:3]=2[S:11][C:12]=1[C:13]([NH2:15])=[O:14]

Participants

6

Reactant 3

HCID 129612-MercaptoacetamideHCID 27612003-Bromo-2-fluorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 442031033-Amino-7-bromobenzo[b]thiophene-2-carboxamideYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-bromo-2-fluoro-benzonitrile (2 g, 10 mmol) in DMF (50 mL) was added 2-mercaptoacetamide (1.2 eq., 12 mL, 100 mg/mL in MeOH-ammonia solution) followed by sodium methoxide (1.2 eq., 24 mL, 0.5 M in MeOH) at room temperature under nitrogen. After 2 h, the resulting homogenous yellow solution was warmed to 70° C. for 17 h. Upon cooling to room temperature, the resulting dark green reaction mixture was concentrated to give a green solid. This solid was diluted with MeOH and collected via filtration to give 2.0 g (74%) of 3-amino-7-bromo-benzo[b]thiophene-2-carboxylic acid amide.

Workup

  1. temperatureUpon cooling to room temperature
  2. concentrationthe resulting dark green reaction mixture was concentrated
  3. customto give a green solid
  4. filtrationcollected via filtration

Sources & evidence

ORD record
ord-ba946fd81798420daff5ec3fecf36246
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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