Potassium thiocyanate → 3-Thiocyanato-2,2-dimethyl-1-propanesulfonamide

HRID 465933Notes

Reaction equation

HRID 465933 reaction equation
S(O[CH2:12][C:13]([CH3:20])([CH3:19])[CH2:14][S:15]([NH2:18])(=[O:17])=[O:16])(C1C=CC(C)=CC=1)(=O)=O.[S-:21][C:22]#[N:23].[K+]>CN(C)C=O>[S:21]([CH2:12][C:13]([CH3:20])([CH3:19])[CH2:14][S:15]([NH2:18])(=[O:16])=[O:17])[C:22]#[N:23]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 100646893-Tosyloxy-2,2-dimethyl-1-propanesulfonamide

Product 1

HCID 104430543-Thiocyanato-2,2-dimethyl-1-propanesulfonamideYield 21.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.2 g of 3-tosyloxy-2,2-dimethyl-1-propanesulfonamide and 3.75 g of potassium thiocyanate in 30 ml of dimethylformamide was stirred at 130°-140° C. for 6 hours, and then concentrated to dryness. A mixture of dichloromethane and methanol (9:1)was added to the residue, followed by filtration to remove insoluble material. The filtrate was concentrated and the residue was subjected to a column chromatography, eluting with chloroform-ethyl acetate (2:1). The relevant fractions were concentrated to obtain 0.87 g of 3-thiocyanato-2,2-dimethyl-1-propanesulfonamide as yellow oil.

Workup

  1. concentrationconcentrated to dryness
  2. additionA mixture of dichloromethane and methanol (9
  3. addition1)was added to the residue
  4. filtrationfollowed by filtration
  5. customto remove insoluble material
  6. concentrationThe filtrate was concentrated
  7. washeluting with chloroform-ethyl acetate (2:1)
  8. concentrationThe relevant fractions were concentrated

Sources & evidence

ORD record
ord-870789b9d8184a9ba1438d557e25e1f5
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Reaction notes

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