Bromoacetic Acid → HCID 10518122, compound

HRID 2226865Notes

Reaction equation

HRID 2226865 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[SH:6][C:7]1[C:8]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:9]=2[S:10][C:11]=1[C:12]([NH2:14])=[O:13].C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[NH2:14][C:12]([C:11]1[S:10][C:9]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:8]=2[C:7]=1[S:6][CH2:2][C:3]([OH:5])=[O:4])=[O:13]

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 516892Sodium BicarbonateHCID 10847601HCID 10847601, compound

Product 1

HCID 10518122HCID 10518122, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromoacetic acid (72 mg, 0.52 mmol) is added to a room temperature solution of 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide (50 mg, 0.21 mmol) in 3 mL of THF followed by NaHCO3 (219 mg, 2.60 mmol) and the reaction mixture is stirred at room temperature for 4 hours. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane provides [[2-(aminocarbonyl)-5-methoxybenzo[b]thien-3-yl]thio]acetic acid in 54% yield; mp=126°-127° C.

Workup

  1. washwashed with 1N HCl 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-35574175c5434aaeadeebe04a9848f17
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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