Water → 5-Amino-2-(1-methyl-4-phenyl-1H-imidazol-5-yl)-1,3-oxazole-4-carbonitrile

HRID 32511

Reaction equation

HRID 32511 reaction equation
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=[CH:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:27][CH:28]([C:31]#[N:32])[C:29]#[N:30].O>CN1C(=O)CCC1>[CH3:7][CH2:6][CH2:5][CH:10]([CH3:15])[CH3:11].[NH2:32][C:31]1[O:8][C:7]([C:6]2[N:2]([CH3:1])[CH:3]=[N:4][C:5]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:27][C:28]=1[C:29]#[N:30]

Participants

6

Reactant 3

HCID 962WaterHCID 563049Aminomalononitrile p-toluenesulphonateHCID 179658201-Methyl-4-phenyl-1H-imidazole-5-carbonyl chloride2×

Product 2

HCID 78922-MethylpentaneHCID 179657695-Amino-2-(1-methyl-4-phenyl-1H-imidazol-5-yl)-1,3-oxazole-4-carbonitrileYield 135.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A suspension of 1-methyl-4-phenyl-1H-imidazole-5-carbonyl chloride (intermediate 4) (0.80 g) in anhydrous NMP (2 mL) was added to aminomalononitrile p-toluenesulfonate (0.92 g) in anhydrous NMP (10 mL). The resultant mixture was stirred for 24 hours. The mixture was poured into water (10 mL), extracted with EtOAc (3×20 mL), organics combined and further washed with water (10 mL), aqueous sodium hydrogen carbonate solution (10 mL) then brine (10 mL). Organics were dried (MgSO4) and evaporated to give a pale gum. Trituration with isohexane (5 mL) gave the title compound as a white solid (650 mg, 68%);

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washfurther washed with water (10 mL), aqueous sodium hydrogen carbonate solution (10 mL)
  3. dry with materialOrganics were dried (MgSO4)
  4. customevaporated
  5. customto give a pale gum

Sources & evidence

ORD record
ord-788ae941d6bc4b03b8f7827949398947
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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