2-Vinylpyridine → HCID 20559434, compound

HRID 224642Notes

Reaction equation

HRID 224642 reaction equation
[Na].[ClH:2].[NH2:3][CH2:4][CH2:5][SH:6].[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[CH2:8]>C(O)C>[ClH:2].[ClH:2].[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:7][CH2:8][S:6][CH2:5][CH2:4][NH2:3]

Participants

5

Reactant 3

HCID 75212-VinylpyridineHCID 9082Cysteamine HydrochlorideHCID 5360545Sodium

Product 1

HCID 20559434HCID 20559434, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium (9.2 g) in ethanol (300 ml) at 5° was added 2-aminoethanethiol hydrochloride (24 g). The solution was stirred at 5°-10° for 1.5 hr, 2-ethenylpyridine (20 g) was added and the mixture refluxed for 16 hr. The cooled mixture was filtered, the filtrate evaporated to dryness and the residue extracted with ether. Excess ethereal hydrogen chloride was added and the gummy precipitate crystallised from methanol-isopropanol to give the title compound (12.5 g) m.p. 151°-154°.

Workup

  1. temperaturethe mixture refluxed for 16 hr
  2. filtrationThe cooled mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. extractionthe residue extracted with ether
  5. additionExcess ethereal hydrogen chloride was added
  6. customthe gummy precipitate crystallised from methanol-isopropanol

Sources & evidence

ORD record
ord-dcaf43d3c571482bb09c238cae51272f
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Reaction notes

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