Dimethyl Sulfoxide → HCID 54096296, compound

HRID 274288Notes

Reaction equation

HRID 274288 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][S:6]([CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12]I)(=[O:8])=[O:7])[CH3:3].[C-:16]#[N:17].[K+].CS(C)=O>O.C1OCCOCCOCCOCCOCCOC1>[C:16]([CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][CH2:9][S:6]([N:5]=[CH:4][N:2]([CH3:3])[CH3:1])(=[O:8])=[O:7])#[N:17]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 53717320HCID 53717320, compound

Product 1

HCID 54096296HCID 54096296, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.85 g of 4-(N,N-dimethylaminomethylene)aminosulfonyl-1-iodo-2,2-dimethylbutane, 0.49 g of potassium cyanide, 0.06 g of 18-crown-6 and 30 ml of dimethyl sulfoxide was stirred at 100° C. for 14 hours. After cooling, the reaction mixture was diluted with 100 ml of water and extracted with ethyl acetate. The extract was washed with water and dried (MgSO4) and the solvent was distilled off. The residue was subjected to silica gel (70 g) column chromatography and elution was carried out with ethyl acetate-hexane (9:1). The fractions containing the objective compound were pooled and concentrated and the residue was recrystallized from ethyl ether to provide 1.11 g of the title compound. m.p. 53°-54° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off
  6. washThe residue was subjected to silica gel (70 g) column chromatography and elution
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated
  9. customthe residue was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-36201999d06c40a5af2d1c6b9ec2f7e1
Source dataset
uspto-grants-1995_02
Patent number
US05389633

Reaction notes

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