Ammonia → HCID 20147704, compound

HRID 543304Notes

Reaction equation

HRID 543304 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(O)(=O)=O.[CH2:12]([NH:20][CH:21](N)[CH3:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C([C:31]#[N:32])C1C=CC=CC=1.N.[OH-].[Na+]>>[CH2:12]([N:20]1[CH2:21][CH2:22][N:32]=[C:31]1[CH2:9][C:8]1[CH:10]=[CH:11][CH:5]=[CH:6][CH:7]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 86741462HCID 86741462, compound

Product 1

HCID 20147704HCID 20147704, compoundYield 98.7%

Conditions

Temperature
50 °C

Procedure

A mixture of N-(n-octyl)-ethanediamine tosylate (10 g, 0.029 mol) and benzyl cyanide (0.9 ml, 0.029 mol) was heated at 200° C. until evolution of ammonia ceased. The reaction mixture was cooled to 50° C. and treated with aqueous sodium hydroxide (15 ml, 5M). The resulting mixture was stirred for 15 minutes and then extracted with dichloromethane. The organic phase was separated, washed with water, and dried over anhydrous magnesium sulphate. Th solvent was removed under reduced pressure to yield a gum which was chromatographed on silica gel using increasing proportions of methanol in dichloromethane to yield 4,5-dihydro-1-n-octyl-2-phenylmethylimidazole (7.8 g) having the formula ##STR24##

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customTh solvent was removed under reduced pressure
  6. customto yield a gum which
  7. customwas chromatographed on silica gel using
  8. temperatureincreasing proportions of methanol in dichloromethane

Sources & evidence

ORD record
ord-76ce0b93e0034340adcc856da0fafd7d
Source dataset
uspto-grants-1987_04
Patent number
US04661602

Reaction notes

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