Sodium Thiosulfate → Ethyl 4-(2-amino-5-bromo-phenylamino)-2-fluoro-benzoate

HRID 1792481Notes

Reaction equation

HRID 1792481 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([F:20])[CH:10]=1.[Br:21]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:21])=[CH:4][C:3]=1[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([F:20])[CH:10]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22031117Ethyl 4-(2-amino-phenylamino)-2-fluoro-benzoate

Product 1

HCID 22031624Ethyl 4-(2-amino-5-bromo-phenylamino)-2-fluoro-benzoateYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

179 mg ethyl 4-(2-amino-phenylamino)-2-fluoro-benzoate (compound in Production Example 332) was dissolved in 4 mL N,N-dimethylformamide, and 116 mg N-bromosuccinimide was added thereto under ice-cooling and stirred for 2 hours. An aqueous sodium thiosulfate solution and an aqueous sodium bicarbonate solution were added thereto and stirred for 1 hour, and the reaction mixture was extracted with ethyl acetate. The extract was purified by NH silica gel chromatography (ethyl acetate/hexane), to give 157 mg of the title compound as a red oil.

Workup

  1. temperatureunder ice-cooling
  2. stirringstirred for 1 hour
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customThe extract was purified by NH silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f76b2293b0184ea5b1efefeb0b0b4eb7
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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