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

HRID 1590058Notes

Reaction equation

HRID 1590058 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 (9:1)
  3. additionwas 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-ce02a5d95bcb44659369984451536e43
Source dataset
uspto-grants-1993_04
Patent number
US05202324

Reaction notes

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