Propyl mercaptan → HCID 21529711, compound

HRID 1657690Notes

Reaction equation

HRID 1657690 reaction equation
[OH-].[K+].Cl[O-].[Na+].[CH2:6]([SH:9])[CH2:7][CH3:8].[C:10]([N:14]=[N:15][C:16](Cl)([CH3:18])[CH3:17])([CH3:13])([CH3:12])[CH3:11].[OH-].[Na+]>O.CO>[C:10]([N:14]=[N:15][C:16]([S:9][CH2:6][CH2:7][CH3:8])([CH3:18])[CH3:17])([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 5

HCID 7848Propyl mercaptanHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 1564434955296-56-5HCID 23665760Sodium Hypochlorite

Product 1

HCID 21529711HCID 21529711, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To 200 ml. of a methanol solution containing 18.2 grams (0.275 moles) of 85% potassium hydroxide pellets in a 11/2 liter jacketed reactor equipped with a mechanical stirrer, thermometer, condenser connected to a bubbler filled with sodium hypochlorite, was added 20.0 grams (0.263 moles) of 1-propanethiol from a pressure equalizing dropping funnel. After the addition of the mercaptan the reaction mixture was stirred for an additional 1/2 hour and then 45.5 grams (0.25 moles) of 88.9% 2-t-butylazo-2-chloropropane was added dropwise over 5 minutes controlling the reaction temperature at 22°C ± 3°C by running cold water through the reactor jacket. The reaction was stirred for an additional 1 hour at 25°C, 5 grams (0.0625 moles) of 50% NaOH added along with 400 mls. of water. The product was extracted with 200 mls. of pentane, the pentane layer separated and washed with 50 ml. of 5% NaOH for 5 minutes, 50 mls. of 10% NaOH for 5 minutes, and then 50 ml. portions of water, 5% HCl, 10% HCl, saturated NaHCO3 solution, dried over anhydrous sodium sulfate, filtered, and the pentane evaporated under reduced pressure to leave 45.9 grams (91.4%) of crude 2-t-butylazo-2-propylthiopropane. Gas chromatographic analysis indicated there was small amounts of 2-t-butylazo-2-methoxypropane and propyl disulfide present in the product.

Workup

  1. customequipped with a mechanical stirrer
  2. customthermometer, condenser connected to a bubbler
  3. customat 22°C ± 3°C
  4. stirringThe reaction was stirred for an additional 1 hour at 25°C
  5. extractionThe product was extracted with 200 mls
  6. customof pentane, the pentane layer separated
  7. washwashed with 50 ml
  8. waitof 5% NaOH for 5 minutes
  9. waitof 10% NaOH for 5 minutes
  10. dry with materialportions of water, 5% HCl, 10% HCl, saturated NaHCO3 solution, dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customthe pentane evaporated under reduced pressure

Sources & evidence

ORD record
ord-f678e7db802c465682d7148f3a1f00d6
Source dataset
uspto-grants-1976_06
Patent number
US03962210

Reaction notes

Loading…