Acetic Acid → HCID 59648651, compound

HRID 1363297Notes

Reaction equation

HRID 1363297 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]=[O:5].S1C2[CH:12]=[C:11]([C:14]([O:16][CH3:17])=O)[NH:10][C:9]=2[CH:8]=[CH:7]1.[OH-:18].[Na+].[C:20](O)(=O)C>>[CH3:1][N:2]([CH2:20][C:7]1[O:5][C:4]2[CH:12]=[C:11]([C:14]([O:16][CH3:17])=[O:18])[NH:10][C:9]=2[CH:8]=1)[CH3:3]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4058811methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 59648651HCID 59648651, compoundYield 36%

Procedure

Under N2, to 9 mL of glacial acetic acid were added N,N-dimethylamine (40% aqueous solution) (437 mg, 9.94 mmol), formaldehyde (37% aqueous solution) (283 mg, 9.90 mmol), and methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (1.64 g, 9.94 mmol). The temperature was kept between 0 and 5° C. while the components were added. The reaction mixture was heated at reflux for 1 h, and was then allowed to stand at rt for 12 h. The mixture was poured onto 30 g of ice, and it was brought to pH 10 by careful addition of 10% sodium hydroxide. The temperature was not allowed to exceed 10° C. while the base was added. The gummy substance solidified when stored in the refrigerator overnight. The solid was collected and dried in vacuo. It was recrystallized from petroleum ether (30-60° C.) to yield methyl 2-[(dimethylamino)methyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (0.80 g, 36%). 1H NMR (400 MHz, CDCl3) δ ppm 2.36 (s, 6H) 3.71 (s, 2H) 3.81 (s, 3H) 6.33 (s, 1H) 6.69 (s, 1H).

Workup

  1. customwas kept between 0 and 5° C. while the components
  2. additionwere added
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 1 h
  5. customto exceed 10° C. while the base
  6. additionwas added
  7. customstored in the refrigerator overnight
  8. customThe solid was collected
  9. customdried in vacuo
  10. customIt was recrystallized from petroleum ether (30-60° C.)

Sources & evidence

ORD record
ord-8573706313244fd88c0581696b5eee5d
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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