Sodium Carbonate → HCID 18963771, compound

HRID 2226860Notes

Reaction equation

HRID 2226860 reaction equation
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[SH:8][C:9]1[C:10]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:11]=2[S:12][C:13]=1[C:14]([NH2:16])=[O:15].C([O-])(O)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[NH2:16][C:14]([C:13]1[S:12][C:11]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:10]=2[C:9]=1[S:8][CH2:7][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[O:15]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 95576Methyl 2-bromopropionate2×HCID 516892Sodium BicarbonateHCID 10847601HCID 10847601, compound

Product 1

HCID 18963771HCID 18963771, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl bromopropionate (75 μL, 0.69 mmol) is added to a room temperature solution of 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide (150 mg, 0.63 mmol) in 7 mL of THF followed by NaHCO3 (334 mg, 3.15 mmol). Additional methyl bromopropionate (150 μL) and Na2CO3 (70 mg) are added and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, water, 1N NaOH, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate: hexane followed by recrystallization from methanol: water gives methyl 3-[[2-(aminocarbonyl)-5-methoxybenzo[b]thien-3-yl]thio]propanoate in 46% yield; mp=142°-144° C.

Workup

  1. washwashed with 1N HCl, water, 1N NaOH, 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
  5. customhexane followed by recrystallization from methanol

Sources & evidence

ORD record
ord-619f9aecb85f4632b0f1bcc59d6cf6d1
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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