Propyl mercaptan → HCID 19863040, compound

HRID 2308591Notes

Reaction equation

HRID 2308591 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([SH:10])[CH2:8][CH3:9].Br[C:12]1[C:16]([Br:17])=[CH:15][S:14][C:13]=1[C:18]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)=O>CN(C)C=O>[Br:17][C:16]1[C:12]([S:10][CH2:7][CH2:8][CH3:9])=[C:13]([CH2:18][C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[S:14][CH:15]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 13924248HCID 13924248, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19863040HCID 19863040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cloudy solution of 80 mL of dimethylformamide containing 3.7 g of potassium-t-butoxide, under a nitrogen blanket and cooled to 0°, was added 3.0 mL of n-propanethiol. This mixture was stirred for 5 minutes and then 12 g of the product of Example 8 was added in one portion. After stirring for 3 hours at room temperature, the mixture was poured into 400 mL of ice-water and extracted with methylene chloride. The organic layer was washed with 1N NaOH (aq), water and dried (MgSO4). Filtration and concentration of the filtrate in vacuo afforded 7.5 g of the subject compound as a dark oil.

Workup

  1. stirringAfter stirring for 3 hours at room temperature
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with 1N NaOH (aq), water
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-8a09ece88ad740f6abdba46be2ff66d1
Source dataset
uspto-grants-1987_09
Patent number
US04690705

Reaction notes

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