Bromoform → 960254-14-2

HRID 1920250Notes

Reaction equation

HRID 1920250 reaction equation
N[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][C:3]=1[C:9]#[N:10].N(OC(C)(C)C)=O.C(Br)(Br)[Br:19]>>[Br:19][C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][C:3]=1[C:9]#[N:10]

Participants

4

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 127307325-amino-1,2-dimethyl-1H-imidazole-4-carbonitrile

Product 1

HCID 23583878960254-14-2Yield 42%

Procedure

A solution of 5-amino-1,2-dimethyl-1H-imidazole-4-carbonitrile (8.5 g, 62 mmol) in bromoform (51 mL) was cooled with an ice water bath, and tert-butyl nitrite (12.87 g, 124.8 mmol) was added dropwise. The reaction was heated on a steam bath for 30 minutes, allowed to cool, and then refrigerated. The solution was decanted to separate it from a precipitate, and then the solution was purified by column chromatography on silica gel (eluting with ethyl acetate) to provide 5.2 g (42%) of 5-bromo-1,2-dimethyl-1H-imidazole-4-carbonitrile as a bright orange solid.

Workup

  1. temperatureThe reaction was heated on a steam bath for 30 minutes
  2. temperatureto cool
  3. customThe solution was decanted
  4. customto separate it from a precipitate
  5. customthe solution was purified by column chromatography on silica gel (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-92a11dcc724e4edf9a3ac9f783bec335
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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