Thionyl Chloride → HCID 21524613, compound

HRID 917970Notes

Reaction equation

HRID 917970 reaction equation
[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([N+:9]([O-:11])=[O:10])[N:4]=[C:3]1[CH2:12]O.S(Cl)([Cl:16])=O>C1C=CC=CC=1>[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([N+:9]([O-:11])=[O:10])[N:4]=[C:3]1[CH2:12][Cl:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14638340HCID 14638340, compound

Product 1

HCID 21524613HCID 21524613, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.6 G. of 1-methyl-2-hydroxymethyl-4-nitro-5-cyanoimidazole is dissolved in 25 ml. of benzene and treated with 2.7 ml. of thionyl chloride. The reaction mixture is refluxed for 1 hour, cooled, filtered and evaporated to dryness. The residue is recrystallized from isopropanol affording 0.6 g. of 1-methyl-2-chloromethyl-4-nitro-5-cyanoimidazole.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue is recrystallized from isopropanol affording 0.6 g

Sources & evidence

ORD record
ord-585c3a7ebd46435e8b6d205946556055
Source dataset
uspto-grants-1976_07
Patent number
US03968228

Reaction notes

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