Ammonia → HCID 11450096, compound

HRID 1594383Notes

Reaction equation

HRID 1594383 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:11]=[N:10][C:9]=1[C:17]([OH:19])=O.C(Cl)(=O)C(Cl)=O.[NH3:26]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[CH:11]=[N:10][C:9]=1[C:17]([NH2:26])=[O:19]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 23073101HCID 23073101, compound

Product 1

HCID 11450096HCID 11450096, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0.2 M solution of 5-(2-bromophenyl)-1-isobutyl-1H-imidazole-4-carboxylic acid (1.42 g; 4.4 mM) in anhydrous THF is added drop by drop, at 0° C., with oxalyl chloride (376 μl; 4.4 mM), then left to react at room temperature for about one hour, thus obtaining 5-(2-bromophenyl)-1-isobutyl-1H-imidazole-4-chlorocarbonyl. The mixture is then added drop by drop with 3 ml of conc. NH3 and reacted for one hour, then extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated under reduced pressure, thereby obtaining 1.14 g of 5-(2-bromophenyl)-1-isobutyl-1H-imidazole-4-carboxamide which is used directly in the subsequent reaction. (Yield: 80.5%).

Workup

  1. customto react at room temperature for about one hour
  2. customreacted for one hour
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-502b083c1fd64975a80c18edbb1e5220
Source dataset
uspto-grants-2007_11
Patent number
US07301027B2

Reaction notes

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