Ethylenediamine → (2'-methoxy-3'-nitro-biphenyl-4-yl]-4,5-dihydro-1H-imidazole

HRID 384358Notes

Reaction equation

HRID 384358 reaction equation
[N+:1]([C:4]1[C:5]([O:18][CH3:19])=[C:6]([C:10]2[CH:15]=[CH:14][C:13](C=O)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:20][CH2:21][CH2:22][NH2:23].BrN1C(=O)CC[C:26]1=O>ClCCl>[CH3:19][O:18][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[C:10]1[CH:11]=[CH:12][C:13]([N:20]2[CH2:21][CH2:22][N:23]=[CH:26]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 67184N-bromobutanimideHCID 574838283'-Nitro-2'-methoxy-biphenyl-4-carbaldehyde

Product 1

HCID 86648899(2'-methoxy-3'-nitro-biphenyl-4-yl]-4,5-dihydro-1H-imidazoleYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3′-nitro-2′-methoxy-biphenyl-4-carbaldehyde 32a (4.0 g, 15.5 mmol) in 40 mL of dichloromethane under stirring, upon cooling by an ice-water bath, was added 1,2-diaminoethane (981 mg, 16.3 mmol). After the mixture was stirred for another 0.5 hours, 1-bromo-pyrrolidine-2,5-dione (2.91 g, 16.33 mmol) was added. Upon completion of the addition, the ice-water bath was removed. The reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 2-[(2′-methoxy-3′-nitro-biphenyl-4-yl]-4,5-dihydro-1H-imidazole 32b (4.0 g, 86.9%) as yellow solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. additionUpon completion of the addition
  3. customthe ice-water bath was removed
  4. stirringThe reaction mixture was stirred overnight at room temperature
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc6bb2781f604a7b81bbc208ddc41186
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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