Dimethylformamide → 2,3-bis(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 2052679Notes

Reaction equation

HRID 2052679 reaction equation
CN(C)C=O.Br[CH:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O.[NH2:26][C:27]1[CH2:31][CH2:30][CH2:29][N:28]=1>O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[N:26]=[C:27]3[CH2:31][CH2:30][CH2:29][N:28]3[C:7]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanoneHCID 127789042-Amino-1-pyrroline

Product 1

HCID 12815562,3-bis(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 ml of dry N,N-dimethylformamide was added 30. g (0.09 mol) of 2-bromo-1,2-di(4-methoxyphenyl)ethanone and 19.5 g (0.27 mol) of 2-amino-4,5-dihydro-3H-pyrrole. The mixture was stirred for three days at 25° with the exclusion of moisture. The reaction mixture was poured into water and the aqueous suspension was extracted three times with methylene chloride. The organic extracts were combined and washed six times with water, then dried (K2CO3). The solvent was evaporated and the residue was recrystallized from chloroform-hexane and dried overnight (80° in vacuo) to give the title compound, m.p. 146°-147.5°.

Workup

  1. extractionthe aqueous suspension was extracted three times with methylene chloride
  2. washwashed six times with water
  3. dry with materialdried (K2CO3)
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from chloroform-hexane
  6. customdried overnight (80° in vacuo)

Sources & evidence

ORD record
ord-08191bfd8ed249808f2354f250ab9e8a
Source dataset
uspto-grants-1980_01
Patent number
US04186205

Reaction notes

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