Pyridine → HCID 18331728, compound

HRID 2270445Notes

Reaction equation

HRID 2270445 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.Cl[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]>C(OCC)(=O)C>[CH:21]([O:20][C:18]([NH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8])=[O:19])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 18331728HCID 18331728, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

22.1 g (0.141 mol) of methyl 3-aminothiophene-2-carboxylate was dissolved in 100 ml of ethyl acetate, and to this was added 11.7 g (0.148 mol) of pyridine. 18.1 g (0.148 mol) of isopropyl chloroformate was added dropwise while cooling with ice over 30 minutes. After completion of the addition, the solution was heated to 60° C. and stirred with heating for 3 hours. After completion of the reaction, the reaction solution was washed sequentially with a 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/3) to obtain 30.6 g of the intended compound as a crystal (yield: 85%). The crystal herein obtained was not analyzed and used for the next reaction.

Workup

  1. temperaturewhile cooling with ice over 30 minutes
  2. additionAfter completion of the addition
  3. temperaturewith heating for 3 hours
  4. customAfter completion of the reaction
  5. washthe reaction solution was washed sequentially with a 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-7c6668c3e88c4908a3a436b1b075add7
Source dataset
uspto-grants-2001_12
Patent number
US06331634B1

Reaction notes

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