Dimethyl Sulfoxide → HCID 14638340, compound

HRID 917969Notes

Reaction equation

HRID 917969 reaction equation
[CH3:1][N:2]1[C:6](S(C)(=O)=O)=[C:5]([N+:11]([O-:13])=[O:12])[N:4]=[C:3]1[CH2:14][OH:15].[C-:16]#[N:17].[K+].CS(C)=O>O>[CH3:1][N:2]1[C:6]([C:16]#[N:17])=[C:5]([N+:11]([O-:13])=[O:12])[N:4]=[C:3]1[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 21524634HCID 21524634, compound

Product 1

HCID 14638340HCID 14638340, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.21 G. (0.01 moles) of 1-methyl-2-hydroxymethyl-4-nitro-5-methylsulfonylimidazole and 0.715 g. of potassium cyanide in 20 ml. of dry dimethylsulfoxide are heated at 100°C. for 30 minutes. The reaction mixture is diluted with an equal volume of water and extracted with ethyl acetate. The combined extracts are dried and evaporated to dryness affording an oily residue which is recrystallized from isopropanol affording 1-methyl-2-hydroxymethyl-4-nitro-5-cyanoimidazole, m.p. 122° to 124°C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined extracts are dried
  3. customevaporated to dryness
  4. customaffording an oily residue which
  5. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-0d22f034e0a4477a8700d670facacf7d
Source dataset
uspto-grants-1976_07
Patent number
US03968228

Reaction notes

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