Butyl iodide → HCID 11458539, compound

HRID 465960Notes

Reaction equation

HRID 465960 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH3:4].[NH2:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([NH:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 11458539HCID 11458539, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

34.1 ml (0.300 mol) of n-butyl iodide was added to a solution of 15.7 g (0.100 mol) of methyl 3-aminothiophene-2-carboxylate and 15.2 g (0.110 mol) of potassium carbonate in 200 ml of N,N-dimethylformamide at 25° C., and the mixture was stirred at 120° C. for 10 hours. After cooling, the solvent was evaporated under reduced pressure and 200 ml of ethyl acetate was added to the residue to remove inorganic salts by filtration. The filtrate was again concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=1/9 v/v) to give 10.2 g (yield: 48%) of methyl 3-(n-butyl)aminothiophene-2-carboxylate (Compound a-1)

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated under reduced pressure and 200 ml of ethyl acetate
  3. additionwas added to the residue
  4. customto remove inorganic salts
  5. filtrationby filtration
  6. concentrationThe filtrate was again concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=1/9 v/v)

Sources & evidence

ORD record
ord-fe93cae47fb64b95b7649391d55ce6a5
Source dataset
uspto-grants-1992_10
Patent number
US05155115

Reaction notes

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