Potassium Carbonate → HCID 22258805, compound

HRID 412229Notes

Reaction equation

HRID 412229 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:24][NH:25][O:26][CH3:27].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(OCC)(=O)C.O.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([N:25]([O:26][CH3:27])[CH3:24])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27667333-(benzyloxy)-2-thiophenecarboxylic acid

Product 1

HCID 22258805HCID 22258805, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(benzyloxy)-2-thiophenecarboxylic acid (3.00 g, 12.81 mmol) in CH2Cl2 (30 mL) were added oxalyl chloride (1.34 mL, 15.4 mmol) and DMF (0.05 mL). The mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (10 mL). Then the solution was added to a mixture of N,O-dimethylhydroxyamine hydrochloride (1.50 g, 15.37 mmol) and K2CO3 (3.54 g, 25.62 mmol) in ethyl acetate (30 mL) and water (30 mL) at 0° C. The mixture was vigorously stirred at 0° C. for 0.5 hrs, and at room temperature for 1.5 hrs. The organic phase was separated, washed with 1 N HCl, saturated NaHCO3, and brine, dried over Na2SO4, filtered, and evaporated. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1) to give 3-(benzyloxy)-N-methoxy-N-methyl-2-thiophenecarboxamide as a pale yellow solid (3.473 g, yield; 98%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  3. stirringThe mixture was vigorously stirred at 0° C. for 0.5 hrs
  4. waitat room temperature for 1.5 hrs
  5. customThe organic phase was separated
  6. washwashed with 1 N HCl, saturated NaHCO3, and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-802b955ef44e425c8b6d6e9ab14025b2
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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