5-Fluoro-2-nitrophenol → N-(2-hydroxy-4-fluorophenyl)-N'-phenylurea

HRID 1956617Notes

Reaction equation

HRID 1956617 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1.[Sn](Cl)Cl.[C:15](=[O:18])(O)[O-].[Na+]>C(O)C>[OH:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[NH:9][C:15]([NH:9][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 24479Stannous ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 15411484N-(2-hydroxy-4-fluorophenyl)-N'-phenylureaYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-2-nitrophenol (500 mg, 3.18 mmol) and tin (II) chloride (1.76 g, 9.2 mmol) in ethanol (10 mL) was heated at 80° C. under argon. After 30 min, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH 7-8), by addition of 5% aqueous sodium bicarbonate, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. Evaporation of the solvent gave the title compound(335 mg, 83%). 1H NMR (CD3 OD/CDCl3): d 6.6 (m, 1H), 6.38 (dd, 1H, J=8.3 Hz and J=2.8 Hz), 6.29 (m, 1H).

Workup

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-60aff74847f34c67b5a7fe94bde70699
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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