Dimethylamine → Methyl 5-(dimethylaminomethyl)-3-thiophenecarboxylate

HRID 851100Notes

Reaction equation

HRID 851100 reaction equation
Cl[CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1.[CH3:12][NH:13][CH3:14]>C(OCC)C>[CH3:12][N:13]([CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1)[CH3:14]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 12926494Methyl 5-(chloromethyl)thiophene-3-carboxylate

Product 1

HCID 12926495Methyl 5-(dimethylaminomethyl)-3-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl 5-(chloromethyl)-3-thiophene-carboxylate (1.9 g) in dry diethylether (100 ml) was treated with anhydrous dimethylamine (5 ml). After 6 hours the solvent was removed in vacuo and the residue was dissolved in 5 M hydrochloric acid (20 ml). The aqueous solution was washed with diethylether, basified with 5 M sodium hydroxide (30 ml) and extracted with ether. The ethereal extracts were evaporated to give an oily residue which was distilled to yield the title compound as a colourless oil (1.6 g) b.p. 120°-130°/0.5 mm.

Workup

  1. customAfter 6 hours the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 5 M hydrochloric acid (20 ml)
  3. washThe aqueous solution was washed with diethylether
  4. extractionextracted with ether
  5. customThe ethereal extracts were evaporated
  6. customto give an oily residue which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-c3bbf6f9cc7b4818a8c860aa6d527a56
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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