Imidazole → HCID 59333320, compound

HRID 1893441Notes

Reaction equation

HRID 1893441 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.I[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[N+:18]([O-:20])=[O:19]>C(OCC)(=O)C>[N+:18]([C:8]1[CH:9]=[C:10]([O:13][C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:12][C:7]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 27826691-iodo-2-nitro-4-(trifluoromethoxy)benzene2×

Product 1

HCID 59333320HCID 59333320, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1H-imidazole (818 mg, 12 mmol, 4 eq) and 1-iodo-2-nitro-4-(trifloromethoxy)benzene (1.0 g, 3 mmol, 1 eq) under argon are heated with a heat-gun at between 300 and 500° C. for 45 min until 1-iodo-2-nitro-4-(trifluoromethoxy)benzene has completely reacted on TLC monitoring. The crude mixture is cooled to room temperature, diluted in ethyl acetate and washed with a saturated solution of ammonium chloride. The organic phase is dried over sodium sulfate and concentrated under vacuum. Purification on silica gel (95/05 dichloromethane/methanol) afforded the title compound (570 mg, 2.08 mmol, 69%) as a yellow powder.

Workup

  1. customhas completely reacted on TLC monitoring
  2. washwashed with a saturated solution of ammonium chloride
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customPurification on silica gel (95/05 dichloromethane/methanol)

Sources & evidence

ORD record
ord-167bd396c2b345b6a74da459aba737ea
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

Loading…