Ethanol → HCID 2807589, compound

HRID 902481Notes

Reaction equation

HRID 902481 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[CH3:10][O:11][C:12]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[NH2:19])=[O:13].N1[CH:25]=[CH:24]C=CC=1.C([OH:28])C>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[NH:19][C:7](=[O:8])[CH2:3][C:4]([O:5][CH2:24][CH3:25])=[O:28])=[O:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 2807589HCID 2807589, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Ethylmalonyl chloride (1.93 mL, 15.22 mmol) was added to a solution of methyl-3-amino-thiophene-2-carboxylate (2 g, 12.70 mmol) in dry toluene (20 mL) and pyridine (1.23 mL, 15.22 mmol) at −10° C. The solution was stirred at −10° C. for 1 h and poured into ice water. The product was extracted by ethyl acetate. The combined organic phase was sequentially washed by diluted HCl solution, saturated NaHCO3 solution, water, and brine. The organic phase was dried over MgSO4 and concentrated to yield an oily residue. The residue was dissolved in hot ethanol and kept overnight at −4° C. The crystals formed were filtered off and filtrate was concentrated to yield 2.2 g (63%) of 3-(2-ethoxycarbonyl-acetylamino)-thiophene-2-carboxylic acid methyl ester as yellow viscous oil. 1H NMR (400 MHz, DMSO-d6) δ 1.21 (t, J=7.2 Hz, 3H), 3.68 (s, 2H), 3.84 (s, 3H), 4.15 (q, J=7.2 Hz, 2H), 7.91 (d, J=5.2 Hz, 1H), 7.93 (d, J=5.2 Hz, 1H), 10.52 (s, 1H) ppm; MS m/z=272 amu (M++1).

Workup

  1. extractionThe product was extracted by ethyl acetate
  2. washThe combined organic phase was sequentially washed by diluted HCl solution, saturated NaHCO3 solution, water, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customto yield an oily residue
  6. waitkept overnight at −4° C
  7. customThe crystals formed
  8. filtrationwere filtered off
  9. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-fad71b9a9abb41ec90e461a56961e6d9
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

Loading…