Isobutylamine → 5-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile

HRID 1920260Notes

Reaction equation

HRID 1920260 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5]C(S(O)(=O)=O)=CC=1.[NH2:12][CH:13]([C:16]#[N:17])[C:14]#[N:15].C(N(CC)CC)C.C(OC)(OC)(OC)CCC.[CH2:35]([NH2:39])[CH:36]([CH3:38])[CH3:37].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[NH2:15][C:14]1[N:39]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:5]([CH2:6][CH2:1][CH3:11])=[N:12][C:13]=1[C:16]#[N:17]

Participants

7

Reactant 5

HCID 6558IsobutylamineHCID 8471Triethylamine2×HCID 10340Sodium CarbonateHCID 1235121,1,1-Trimethoxybutane2×HCID 563049Aminomalononitrile p-toluenesulphonate

Product 1

HCID 585001355-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrileYield 70.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Aminomalononitrile p-toluenesulfonate (25.33 g, 0.100 mol), triethylamine (10.12 g, 0.100 mol), and trimethyl orthobutyrate (14.82 g, 0.11 mol) were combined in toluene (250 mL) and the solution was heated at 60° C. for 1.75 hours. Additional trimethyl orthobutyrate (1.0 mL) was added, and the reaction was allowed to cool over a period of 1.5 hours to 22° C. and further cooled to about 3° C. Triethylamine (10.12 g, 0.100 mol) and isobutylamine (7.32 g, 0.100 mol) were sequentially added, and the reaction was warmed to room temperature slowly and stirred overnight. The reaction mixture was shaken with 10% w/w aqueous sodium carbonate (250 mL), and the mixture was allowed to stand for two hours. A precipitate was present and was isolated by filtration, washed sequentially with toluene and water, air-dried, and further dried under vacuum at 75° C. for 22 hours to provide 14.5 g (70%) of 5-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile as a beige solid, mp 135.0-136.0° C.

Workup

  1. temperatureto cool over a period of 1.5 hours to 22° C.
  2. temperaturefurther cooled to about 3° C
  3. temperaturethe reaction was warmed to room temperature slowly
  4. waitto stand for two hours
  5. customwas isolated by filtration
  6. washwashed sequentially with toluene and water
  7. customair-dried
  8. customfurther dried under vacuum at 75° C. for 22 hours

Sources & evidence

ORD record
ord-91d9ce68f6314aa482567aa1e787d17b
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

Loading…