Ammonia → HCID 178442465, compound

HRID 216350Notes

Reaction equation

HRID 216350 reaction equation
[CH3:1][C:2]([CH3:8])([CH:6]=[CH2:7])[CH2:3][CH:4]=O.[NH3:9].CC1C=CC(S([CH2:20][N+:21]#[C-:22])(=O)=O)=CC=1>CO>[CH3:1][C:2]([CH3:8])([CH:6]=[CH2:7])[CH2:3][C:4]1[N:9]=[CH:20][NH:21][CH:22]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 161915Tosylmethyl isocyanideHCID 129170803,3-Dimethylpent-4-enal

Product 1

HCID 178442465HCID 178442465, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

At 30° C., 3,3-dimethylpent-4-enal (126 g, 0.34 mol) was added over 20 minutes to an ambient temperature, saturated solution of ammonia in methanol (2.7 L). After stirring at 40° C. for 30 minutes, TosMIC (67 g, 0.4 mol) was added. After stirring at reflux overnight, the reaction mixture was concentrated, dissolved in ether and poured into 2N ammonium hydroxide (1500 mL) and stirred. The aqueous phase was extracted with ether. The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo to afford 4-(2,2-dimethylbut-3-en-1-yl)-1H-imidazole which was used in the subsequent step without further purification.

Workup

  1. stirringAfter stirring
  2. temperatureat reflux overnight
  3. concentrationthe reaction mixture was concentrated
  4. dissolutiondissolved in ether
  5. additionpoured into 2N ammonium hydroxide (1500 mL)
  6. stirringstirred
  7. extractionThe aqueous phase was extracted with ether
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41034a33da304415aabf4d938d1a54c2
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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