Propyl mercaptan → HCID 14346837, compound

HRID 2232021Notes

Reaction equation

HRID 2232021 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].CC(C)([O-])C.[K+].[F:11][CH:12]([F:25])[N:13]([CH3:24])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Cl)(=[O:16])=[O:15]>CN(C=O)C>[F:11][CH:12]([F:25])[N:13]([CH3:24])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:4][CH2:1][CH2:2][CH3:3])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 21284138HCID 21284138, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14346837HCID 14346837, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 14.62 ml of n-propylmercaptan, 16.3 g of potassium t-butoxide and 400 ml of DMF at 0° C. was added 27.45 g (0.1076 mole) of N-difluoromethyl-N-methyl-2-chlorobenzenesulfonamide in 100 ml of DMF. The reaction mixture was stirred at room temperature for 2 days and then at 60° C. for 4 hours. The mixture was then concentrated and the residue was partitioned between 1N HCl solution and methylene chloride. The organic layer was separated, dried over MgSO4, and concentrated. The residue was chromatographed on silica gel (Hexane/chloroform 3:2) to yield 24.63 g of N-difluoromethyl-N-methyl-2-(n-propylthio)benzenesulfonamide as an oil.

Workup

  1. waitat 60° C. for 4 hours
  2. concentrationThe mixture was then concentrated
  3. customthe residue was partitioned between 1N HCl solution and methylene chloride
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (Hexane/chloroform 3:2)

Sources & evidence

ORD record
ord-4a36df6ce90942e181bd793ba52f401d
Source dataset
uspto-grants-1988_11
Patent number
US04786316

Reaction notes

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