Cysteamine → 3-Nitro-2-pyridinesulfenyl-ethylamine

HRID 2220046Notes

Reaction equation

HRID 2220046 reaction equation
[N+:1]([C:4]1[C:5]([S:10]Cl)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:12][CH2:13][CH2:14]S>C(O)=O>[N+:1]([C:4]1[C:5]([S:10][CH2:14][CH2:13][NH2:12])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6058CysteamineHCID 1292833-Nitro-2-pyridinesulfenyl

Product 1

HCID 692563493-Nitro-2-pyridinesulfenyl-ethylamine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The 3-nitro-2-pyridinesulfenyl chloride was added to a solution of 2-aminoethanethiol (4.1 grams, 36.19 mmol) in 230 mL of 90% formic acid. The solution was vigorously stirred for one hour. The resulting precipitate was removed by filtration, and a large volume of diethylether was added to the supernatant. The precipitate was collected, dissolved in warm methanol, and reprecipitated with diethyl ether. 3-Nitro-2-pyridinesulfenyl-ethylamine was obtained in 68% overall yield.

Workup

  1. customThe resulting precipitate was removed by filtration
  2. additiona large volume of diethylether was added to the supernatant
  3. customThe precipitate was collected
  4. dissolutiondissolved in warm methanol
  5. customreprecipitated with diethyl ether

Sources & evidence

ORD record
ord-5fe4e2f0a450408aad0bf551dc84e485
Source dataset
uspto-grants-2008_08
Patent number
US07417021B2

Reaction notes

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