Butyl iodide → HCID 11458539, compound

HRID 1742820Notes

Reaction equation

HRID 1742820 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH2:18][CH2:19][CH3:20]>CN(C)C=O>[CH2:17]([NH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8])[CH2:18][CH2:19][CH3:20]

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

To 200 ml of an N,N-dimethylformamide solution containing 15.7 g (0.100 mol) of methyl 3-aminothiophene-2-carboxylate and 15.2 g (0.110 mol) of potassium carbonate was added 34.1 ml (0.300 tool) of n-butyl iodide at 25° C., and the mixture was stirred at 120° C. for 10 hours. After cooling, the solvent was distilled off under reduced pressure, and 200 ml of ethyl acetate was added thereto, and then the inorganic salt was filtered off. The filtrate was concentrated also under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 10.2 g (48%) of Compound (a-1).

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off under reduced pressure, and 200 ml of ethyl acetate
  3. additionwas added
  4. filtrationthe inorganic salt was filtered off
  5. concentrationThe filtrate was concentrated also under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b526873ea9384d229548c3a740f8d5fa
Source dataset
uspto-grants-1994_08
Patent number
US05342843

Reaction notes

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