Imidazole → 1-[1-(4-nitrophenyl)pyrrolid-3-yl]-1H-imidazole

HRID 719675Notes

Reaction equation

HRID 719675 reaction equation
CS(O[CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][CH:6]([N:20]3[CH:24]=[CH:23][N:22]=[CH:21]3)[CH2:7]2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 795ImidazoleHCID 120678141-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonate

Product 1

HCID 121165311-[1-(4-nitrophenyl)pyrrolid-3-yl]-1H-imidazoleYield 73.2%

Procedure

22 g (0.0767 mol) of 1-(4-nitrophenyl)pyrrolid-3-yl methanesulphonate (2) were heated at 95° C. for 2 hours in 170 g of imidazole (2.5 mol), This mixture was poured into 1 l of ice-cold water until crystallization takes place. After filtration and drying, the yellow powder obtained was chromatographed, eluting with dichloromethane, and 14.5 g of derivative (3) were recovered (73.2% yield).

Workup

  1. filtrationAfter filtration
  2. customdrying
  3. customthe yellow powder obtained
  4. customwas chromatographed
  5. washeluting with dichloromethane, and 14.5 g of derivative (3)
  6. customwere recovered (73.2% yield)

Sources & evidence

ORD record
ord-7d5cf7763d9040a59c012f6d3a6a2ef1
Source dataset
uspto-grants-2006_11
Patent number
US07132534B2

Reaction notes

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