Dimethylformamide → HCID 14638338, compound

HRID 917966Notes

Reaction equation

HRID 917966 reaction equation
[CH3:1][N:2]1[C:6](Br)=[C:5]([N+:8]([O-:10])=[O:9])[N:4]=[C:3]1[CH2:11][O:12][C:13](=[O:15])[CH3:14].[CH3:16][N:17](C)C=O>>[CH3:1][N:2]1[C:6]([C:16]#[N:17])=[C:5]([N+:8]([O-:10])=[O:9])[N:4]=[C:3]1[CH2:11][O:12][C:13](=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 21524651HCID 21524651, compound

Product 1

HCID 14638338HCID 14638338, compound

Procedure

2.78 G. (0.01 moles) of 1-methyl-2-acetoxymethyl-4-nitro-5-bromoimidazole and 0.0115 moles of cupric cyanide are combined in 20 ml. of dimethylformamide and heated on a steam bath for 12 hours. The reaction mixture is cooled and poured into 200 ml. of 3% aqueous ammonia and extracted with chloroform. The extracts are washed with water, dried and evaporated under a high vacuum. The residue is recrystallized from isopropanol affording 1.0 g. 1-methyl-2-acetoxymethyl-4-nitro-5-cyanoimidazole, m.p. 92° to 93°C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured into 200 ml
  3. extractionof 3% aqueous ammonia and extracted with chloroform
  4. washThe extracts are washed with water
  5. customdried
  6. customevaporated under a high vacuum
  7. customThe residue is recrystallized from isopropanol affording 1.0 g

Sources & evidence

ORD record
ord-373f0588d0884b6bbd4b16e76589413b
Source dataset
uspto-grants-1976_07
Patent number
US03968228

Reaction notes

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