Water → 2,3-Di(4-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 2052681Notes

Reaction equation

HRID 2052681 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.[NH2:19][C:20]1[CH2:24][CH2:23][CH2:22][N:21]=1.O>CN(C)C=O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:19]=[C:20]3[CH2:24][CH2:23][CH2:22][N:21]3[C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 112216182-Bromo-1,2-di-(4-chlorophenyl)ethanoneHCID 127789042-Amino-1-pyrroline

Product 1

HCID 203763822,3-Di(4-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.2 g (0.018 mol) of 2-bromo-1,2-di-(4-chlorophenyl)ethanone and 4.6 g (0.054 mol) of 2-amino-4,5-dihydro-3H-pyrrole in 60 ml of dry N,N-dimethylformamide was stirred at 25° with exclusion of water for five days. The mixture was then poured into water and the aqueous solution was extracted three times with methylene chloride. The extracts were combined and washed eight times with water, dried (K2CO3) and evaporated. The residue was chromatographed on silica gel (dry column) with 1% tetrahydrofuran in chloroform and 5% tetrahydrofuran in chloroform as eluants. The product-containing section was washed with methanol to remove the product which was, after evaporation of the methanol, recrystallized from methanol-water to give the title compound, m.p. 189°-192°.

Workup

  1. extractionthe aqueous solution was extracted three times with methylene chloride
  2. washwashed eight times with water
  3. dry with materialdried (K2CO3)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (dry column) with 1% tetrahydrofuran in chloroform and 5% tetrahydrofuran in chloroform as eluants
  6. washThe product-containing section was washed with methanol
  7. customto remove the product which
  8. customafter evaporation of the methanol
  9. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-b27348e49ad0486296df5e9036eb4ae7
Source dataset
uspto-grants-1980_01
Patent number
US04186205

Reaction notes

Loading…