Propyl mercaptan → HCID 13924249, compound

HRID 1164739Notes

Reaction equation

HRID 1164739 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([SH:10])[CH2:8][CH3:9].Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)=[O:19]>CN(C)C=O>[CH2:7]([S:10][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)=[O:19])[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 12525776HCID 12525776, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13924249HCID 13924249, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cloudy solution of 400 mL of dry dimethylformamide containing 224 g or potassium-t-butoxide, cooled to 0° under a nitrogen atmosphere, was added 18 mL of n-propanethiol dropwise at such a rate to maintain the temperature below 5° C. The resulting mixture was stirred for 5 minutes and then a solution of 44 g of the product of Example 1 dissolved in 100 mL of dimethylformamide was added. The reaction mixture was stirred for 24 hours at room temperature, poured into 2 L of ice-water and extracted with methylene chloride. The organic layer was separated, washed with 1N NaOH (aq), water, and dried (MgSO4). Filtration, followed by concentration of the filtrate in vacuo gave a dark residue which after column chromatography on silica (methylene chloride as eluant) provided 40 g of the subject compound as a red oil.

Workup

  1. temperatureto maintain the temperature below 5° C
  2. additionwas added
  3. stirringThe reaction mixture was stirred for 24 hours at room temperature
  4. extractionextracted with methylene chloride
  5. customThe organic layer was separated
  6. washwashed with 1N NaOH (aq), water
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration
  9. customgave a dark residue which after column chromatography on silica (methylene chloride as eluant)

Sources & evidence

ORD record
ord-387d80c7bee24c2881c33592f46573f3
Source dataset
uspto-grants-1990_03
Patent number
US04906283

Reaction notes

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