Imidazole → 2-Amino-5-(4-[1-imidazolyl]-phenylsulfonyloxy)nitro-benzene

HRID 1823763Notes

Reaction equation

HRID 1823763 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 120188434-Amino-3-nitrophenyl 4-fluorobenzenesulfonate

Product 1

HCID 221470072-Amino-5-(4-[1-imidazolyl]-phenylsulfonyloxy)nitro-benzeneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.6 g of 2-amino-5-(4-fluorophenylsulfonyloxy)nitrobenzene were combined with 20.7 g imidazole in 100 ml dimethylformamide in a round bottom flask. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. Reaction mixture was then precipitated by addition of water filtered and precipitate was washed with water and dried. Residue was resolubilized in hot ethyl glycol, crystallized by cooling and the crystals were washed with methanol and dried, yielding 10.4 g of 2-amino-5-(4-[1-imidazolyl]-phenylsulfonyloxy)nitro-benzene (melting point 209° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customReaction mixture
  4. customwas then precipitated by addition of water
  5. filtrationfiltered
  6. washprecipitate was washed with water
  7. customdried
  8. customcrystallized
  9. temperatureby cooling
  10. washthe crystals were washed with methanol
  11. customdried

Sources & evidence

ORD record
ord-3ea7af849d4744a8acf784f28da004e9
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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