Triethylamine → Methyl 2-pentanoylaminothiophene-3-carboxylate

HRID 1440796

Reaction equation

HRID 1440796 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:8][C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C(N(CC)CC)C>ClC(Cl)C>[C:1]([NH:8][C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 78381Methyl 2-amino-3-thenoate

Product 1

HCID 18982094Methyl 2-pentanoylaminothiophene-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Valeryl chloride (1.3 g) was added to a solution of methyl 2-aminothiophene-3-carboxylate (1.6 g) [Y. Kuwada et al. Chem. Abst. 82, 156252(1975)] and triethylamine (1.2 g) in dichloroethane (20 ml) under ice-cooling. The mixture was stirred for two hours. The reaction mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as a colorless oil (2.3 g, 96%).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a8d80564f5a44863b04abaf178b07cb0
Source dataset
uspto-grants-1996_03
Patent number
US05500427

Linked notes

Loading…