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

HRID 2052682Notes

Reaction equation

HRID 2052682 reaction equation
Cl[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH2:21][C:22]1[CH2:26][CH2:25][CH2:24][N:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:21]=[C:22]3[CH2:26][CH2:25][CH2:24][N:23]3[C:2]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 127789042-Amino-1-pyrrolineHCID 214086642-Chloro-1,2-di(4-methylthiophenyl)ethanone

Product 1

HCID 203763792,3-Di(4-methylthiophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 9.0 g (0.028 mol) of 2-chloro-1,2-di(4-methylthiophenyl)ethanone in 50 ml of dry N,N-dimethylformamide was added 7.0 g (0.084 mol) of 2-amino-4,5-dihydro-3H-pyrrole. The mixture was stirred for 48 hours at ambient temperature, then poured into 1 liter of ice containing 300 ml of 5% aqueous sodium carbonate solution. The precipitate was collected by filtration and dissolved in methylene chloride. The solution was washed with water, dried (K2CO3) and evaporated to give a residue which was chromatographed on alumina and eluted with methylene chloride-methanol (95:5) to give the title compound, m.p. 127°-128°.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in methylene chloride
  3. washThe solution was washed with water
  4. dry with materialdried (K2CO3)
  5. customevaporated
  6. customto give a residue which
  7. customwas chromatographed on alumina
  8. washeluted with methylene chloride-methanol (95:5)

Sources & evidence

ORD record
ord-ca8d626659224ca89c9f6591e41b1ac8
Source dataset
uspto-grants-1980_01
Patent number
US04186205

Reaction notes

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