Triethylamine → 2-{4-[4-(3,4-Dichloro-phenyl)-butyl]-phenylamino}-5-nitro-benzoic acid

HRID 488507Notes

Reaction equation

HRID 488507 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH:18]=[CH:19][C:20]=1[Cl:21].CCN(CC)CC>C(#N)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:2]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])=[CH:30][CH:31]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 136560814-[4-(3,4-Dichlorophenyl)butyl]phenylamine

Product 1

HCID 222698092-{4-[4-(3,4-Dichloro-phenyl)-butyl]-phenylamino}-5-nitro-benzoic acidYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-fluoro-5-nitrobenzoic acid (1.85 g, 0.01 mol), 4-[4-(3,4-dichlorophenyl)butyl]-phenylamine (2.94 g, 0.01 mol) and Et3N (2.80 mL) in acetonitrile (110 mL) was heated to reflux for 48 hours. The reaction mixture was cooled and concentrated in vacuo to remove the solvent. The residue was dissolved in CH2C2 and washed with diluted HCl. The organic layer was dried Na2SO4), concentrated in vacuo to give a crude solid. Purification by flash chromatography (silica gel, CH2Cl2) yielded 1.40 g (0.003 mol, 30%) of the desired product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customto remove the solvent
  6. dissolutionThe residue was dissolved in CH2C2
  7. washwashed with diluted HCl
  8. concentrationconcentrated in vacuo
  9. customto give a crude solid
  10. customPurification by flash chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-dfcd1b1382264f4f813127a9b6ca8e7f
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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