Benzoyl chloride → 2-Phenyl-1-benzofuran-5-amine

HRID 2243097Notes

Reaction equation

HRID 2243097 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[C:9]1([C:8]2[O:15][C:10]3[CH:11]=[CH:7][C:6]([NH2:3])=[CH:14][C:9]=3[CH:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 167651722-Phenyl-1-benzofuran-5-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Triethylamine (63.4 ml, 0.455 mol) is added to 2-hydroxy-5-nitrobenzylphsophonium bromide (50 g, 0.101 mol) in refluxing toluene (600 ml), followed by addition of benzoyl chloride (16.2 ml, 0.140 mol) in toluene (50 ml). The mixture is refluxed for 3 hours, cooled and stirred at room temperature for 2 hours. The resulting mixture is concentrated and the product is recrystallized from 2/1 isopropyl ether/hexane, and the 2-phenyl-5-nitrobenzofuran is filtered off. This product is hydrogenated in THF (300 ml) and methanol (150 ml), with Pd/C (10%; 3.2 g). The catalyst is filtered off and the filtrate is concentrated. The residue is taken up in isopropanol/MeOH/HCl, and the hydrochloride is precipitated. It is suspended in 1M NaOH and extracted with ethyl acetate. The extracts are washed with water and concentrated. The solid is recrystallized from isopropyl ether. Yield: 9.8 g (32%); Elem. anal. C14H11NO; theory C, 80.36; H, 5.30; N, 6.70. found C, 79.78; H, 5.16; N, 6.87. IR (KBr): 3400, 3325, 1595, 1465 cm−1.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. temperaturecooled
  3. concentrationThe resulting mixture is concentrated
  4. customthe product is recrystallized from 2/1 isopropyl ether/hexane
  5. filtrationthe 2-phenyl-5-nitrobenzofuran is filtered off
  6. filtrationThe catalyst is filtered off
  7. concentrationthe filtrate is concentrated
  8. customthe hydrochloride is precipitated
  9. extractionextracted with ethyl acetate
  10. washThe extracts are washed with water
  11. concentrationconcentrated
  12. customThe solid is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-82959601dc014c5794cdf26420103e0b
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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