Ethylamine → HCID 15790198, compound

HRID 1080893Notes

Reaction equation

HRID 1080893 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH2:18])[CH3:17]>O>[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:18][CH2:16][CH3:17])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 13291139HCID 13291139, compound

Product 1

HCID 15790198HCID 15790198, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of 2-benzylthio-6-bromopyridine, 70 ml of a 40% ethylamine aqueous solution, and a catalytic amount of cuprous chloride was allowed to react in an autoclave at 180° for 4 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with methylene chloride. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/19 by volume) to obtain 5.9 g of 2-benzylthio-6-ethylaminopyridine as an oily substance.

Workup

  1. customto react in an autoclave at 180° for 4 hours
  2. customAfter completion of the reaction
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/19 by volume)

Sources & evidence

ORD record
ord-002b73dfc3fc4ef5b726530420ce0c77
Source dataset
uspto-grants-1996_12
Patent number
US05583231

Reaction notes

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