Ammonia → HCID 178442466, compound

HRID 216348Notes

Reaction equation

HRID 216348 reaction equation
CC1C=CC(S([CH2:11][N+:12]#[C-:13])(=O)=O)=CC=1.[NH3:14].[CH3:15][C:16]([CH3:22])([CH2:20][CH3:21])[CH2:17][CH:18]=O.Cl>CO>[CH3:15][C:16]([CH3:22])([CH2:20][CH3:21])[CH2:17][C:18]1[N:14]=[CH:11][NH:12][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 161915Tosylmethyl isocyanideHCID 3724921118993-47-8

Product 1

HCID 178442466HCID 178442466, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

TosMIC (154 g, 0.9 mol) was added to an ambient temperature, saturated solution of ammonia in methanol (7 L). After stirring at ambient temperature for 1 h, 3,3-dimethylpentanal (ca. 0.6 mol) was added over 20 min. After stirring at reflux for 3 h, the reaction mixture was poured into cold 1 N hydrochloric acid and washed with hexane. The aqueous layer was basified with 10 N aqueous sodium hydroxide and extracted with ether. The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 5-10% methanol/methylene chloride afforded 4-(2,2-dimethylbutyl)-1H-imidazole.

Workup

  1. stirringAfter stirring
  2. temperatureat reflux for 3 h
  3. washwashed with hexane
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-573d48c680b94777bb80614644ff0e99
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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