Propionic Acid → Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

HRID 502541

Reaktionsgleichung

Reaktionsgleichung von HRID 502541
[C:1]([OH:5])(=O)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:23]([N:25](CC)CC)C.[NH2:30][C:31]1[S:32][CH:33]=[C:34]([CH3:41])[C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1(C)C=CC=CC=1>[CH3:41][C:34]1[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:31]([NH:30][C:1]([NH:25][CH3:23])=[O:5])[S:32][CH:33]=1

Komponenten

6

Edukt 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

Produkt 1

HCID 15085569Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of propionic acid (3.8 ml, 50.64 mmol), diphenylphosphoryl azide (10.9 ml, 50.64 mmol), and triethylamine (7.1 ml, 50.64 mmol) in toluene (30 ml) was refluxed for 1 hour. After cooling to room temperature, ethyl 2-amino-4-methylthiophene-3-carboxylate (3.13 g, 16.88 mmol) was added, and the mixture was refluxed for 18 hours. The product was partitioned between ethyl acetate and water, the organic layer washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with ethyl acetate/hexane 1:1, to provide ethyl 4-methyl-2-[(methylamino)carbonylamino]-thiophene-3-carboxylate as pink crystals.

Aufarbeitung

  1. temperaturewas refluxed for 1 hour
  2. temperaturethe mixture was refluxed for 18 hours
  3. customThe product was partitioned between ethyl acetate and water
  4. washthe organic layer washed with brine
  5. dry with materialdried over sodium sulfate, and solvent
  6. customremoved under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with ethyl acetate/hexane 1:1

Quellen und Nachweise

ORD-Eintrag
ord-d342891077d542e0be0f599352023051
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776868B2

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