Dimethylamine → 5-(Hydroxymethyl)-N,N-dimethyl-3-thiophenecarboxamide

HRID 851103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851103
[OH:1][CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10]C)=O)[CH:4]=1.C[O-].[Na+].[CH3:15][NH:16][CH3:17]>CO>[OH:1][CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([N:16]([CH3:17])[CH3:15])=[O:10])[CH:4]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 10942334Sodium MethoxideHCID 12926498Methyl 5-(hydroxymethyl)thiophene-3-carboxylate

Produkt 1

HCID 212890685-(Hydroxymethyl)-N,N-dimethyl-3-thiophenecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-(hydroxymethyl)-3-thiophenecarboxylate (3 g), sodium methoxide (0.2 g) and excess anhydrous dimethylamine in dry methanol (20 ml) was stirred for 24 h at ambient temperature. The solvent was removed in vacuo, water was added and the product was extracted with ethyl acetate. The organic extract was evaporated to leave an oily residue which was chromatographed on silica with ethyl acetate-light petroleum 40°-60°; (1:1) to give the title compound (1.3 g). I.R. (CHBr3) OH 3,595 cm-1 ; C=O 1,620 cm-1

Aufarbeitung

  1. customThe solvent was removed in vacuo, water
  2. additionwas added
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe organic extract
  5. customwas evaporated
  6. customto leave an oily residue which
  7. customwas chromatographed on silica with ethyl acetate-light petroleum 40°-60°

Quellen und Nachweise

ORD-Eintrag
ord-60d94c14d304497d8dbe38bfd2292430
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382929

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