2-Mercaptoacetamide → HCID 11485975, compound

HRID 2054913Notes

Reaction equation

HRID 2054913 reaction equation
F[C:2]1[C:9]([I:10])=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#[N:5].[SH:15][CH2:16][C:17]([NH2:19])=[O:18].C[O-].[Na+]>CO>[NH2:5][C:4]1[C:3]2[C:6]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:8]=[C:9]([I:10])[C:2]=2[S:15][C:16]=1[C:17]([NH2:19])=[O:18]

Participants

5

Reactant 3

HCID 129612-MercaptoacetamideHCID 10942334Sodium MethoxideHCID 59656661HCID 59656661, compound

Product 1

HCID 11485975HCID 11485975, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the above benzonitrile intermediate (140 mg, 0.444 mmol) in 4 mL of MeOH was added 2-mercaptoacetamide (100 mg/mL in MeOH-ammonia solution) (0.49 mL, 0.533 mmol) and 0.5M sodium methoxide in MeOH (1.78 mL, 0.89 mmol). The reaction mixture was stirred at room temperature for 18 h. The mixture was concentrated and purified by silica gel chromatography eluting with 2-5% MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 79 mg (46%) of 3-amino-7-iodo-4-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid amide as a yellow crystalline solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography
  3. washeluting with 2-5% MeOH/CH2Cl2
  4. customThe product fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e87916cb566d4ee880f608cadf0d6395
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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