Dichloromethane → N-(2-Sulfanylethyl)pentanamide

HRID 1255371Notes

Reaction equation

HRID 1255371 reaction equation
Cl.[SH:2][CH2:3][CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].[C:12](Cl)(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16].ClCCl>O>[SH:2][CH2:3][CH2:4][NH:5][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9082Cysteamine HydrochlorideHCID 11430Potassium CarbonateHCID 61186Valeryl chloride

Product 1

HCID 22222175N-(2-Sulfanylethyl)pentanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen atmosphere, 22.7 g of 2-mercaptoethylamine hydrochloride (0.2 mol) and 44.3 g of potassium carbonate (0.32 mol) were introduced at room temperature in solution in 130 ml of water. The solution was warmed to 40° C. and 12.0 g of valeryl chloride (0.1 mol) were added dropwise over the course of 15 minutes. The batch was stirred at 40° C. for 3 hours and then cooled to room temperature. 70 ml of dichloromethane were added and a phase separation was carried out. The organic phase was washed with 50 ml of 20% strength ammonium chloride solution, dried over sodium sulfate and freed of its solvent under reduced pressure.

Workup

  1. temperaturecooled to room temperature
  2. customa phase separation
  3. washThe organic phase was washed with 50 ml of 20% strength ammonium chloride solution
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-f51eeac01e55452eae8f120abb552573
Source dataset
uspto-grants-2013_06
Patent number
US08460445B2

Reaction notes

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