Phenylacetic Acid → HCID 54319241, compound

HRID 2392710Notes

Reaction equation

HRID 2392710 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[Cl:15][C:16]1[C:22]([Cl:23])=[CH:21][C:19]([NH2:20])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1>C(O)C>[Cl:15][C:16]1[C:22]([Cl:23])=[CH:21][C:19]([NH:20][C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 24386Thionyl ChlorideHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 54319241HCID 54319241, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of phenylacetic acid (10 mmol) in SOCl2 (4 ml, apr. 50 mmol) was stirred for 16 h at room temperature, then evaporated and kept at 2 mm Hg for 0.5 h to remove residual SOCl2. A suspension of 4,5-dichloro-2-nitroaniline (1.035 g, 5 mmol) in ethanol-free CHCl3 (10 mL) was added to the residue and the mixture was stirred at 50° C. for 4 h. It was then cooled to room temperature and evaporated. The residue was treated with ether (100 mL). Precipitated crude product was filtered, washed with ether (5×20 mL) and dried on air to give the title compound. Yield 90%; mp 116°-118° C. (from EtOH); (Lit., 118° C., Ahmad, Yu., et al., Tetrahedron 21:861 (1965)).

Workup

  1. customevaporated
  2. waitkept at 2 mm Hg for 0.5 h
  3. customto remove residual SOCl2
  4. additionwas added to the residue
  5. stirringthe mixture was stirred at 50° C. for 4 h
  6. temperatureIt was then cooled to room temperature
  7. customevaporated
  8. additionThe residue was treated with ether (100 mL)
  9. customPrecipitated crude product
  10. filtrationwas filtered
  11. washwashed with ether (5×20 mL)
  12. customdried on air

Sources & evidence

ORD record
ord-4ffc10ca3ae344beb56af180890eadcc
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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