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

HRID 867919Notes

Reaction equation

HRID 867919 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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°

Sources & evidence

ORD record
ord-d2951505e7b1467cb66fc06fb592510c
Source dataset
uspto-grants-1988_10
Patent number
US04777179

Reaction notes

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