Hydrochloric Acid → HCID 14458994, compound

HRID 569810Notes

Reaction equation

HRID 569810 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[F:14][C:15]1[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].C(OCC)(=O)C.Cl>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([I:23])=[CH:22][C:15]=2[F:14])=[O:8])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 37744674-Bromo-2-nitrobenzoic acidHCID 19838807HCID 19838807, compound

Product 1

HCID 14458994HCID 14458994, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-bromo-2-nitrobenzoic acid (3.0 g) and N,N'-carbonyldiimidazole (2.37 g) in tetrahydrofuran (30 ml) was stirred at room temperature for 4 hours. To this mixture was added a solution of 2-fluoro-4-iodobenzylamine (3.37 g) in tetrahydrofuran (10 ml), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and 0.5N hydrochloric acid. The organic layer was separated, washed successively with water, aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was removed in vacuo and the crystalline residue was recrystallized from a mixture of ethyl acetate and hexane to give 4-bromo-N-(2-fluoro-4-iodobenzyl)-2-nitrobenzamide (4.88 g).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. washwashed successively with water, aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe crystalline residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-876a774640e54bb1bbc6d393e6736aa0
Source dataset
uspto-grants-1988_03
Patent number
US04734419

Reaction notes

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