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

HRID 652089Notes

Reaction equation

HRID 652089 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-thiophenecarboxylate (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 5M hydrochloric acid (20 ml). The aqueous solution was washed with diethylether, basified with 5M 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 5M 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-392480a0e4534f8faa1a10ed57b3d187
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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