Sodium Dithionite → N-(3-aminophenyl)-3-(trifluoromethyl)benzamide

HRID 1800478Notes

Reaction equation

HRID 1800478 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.O>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 531812HCID 531812, compound

Product 1

HCID 20117519N-(3-aminophenyl)-3-(trifluoromethyl)benzamideYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-nitrophenyl)-3-(trifluoromethyl)benzamide (30.0 g, 96.7 mmol) in tetrahydrofuran (300 mL) was slowly added with heating under reflux, a solution (500 mL) of sodium hydrosulfite (97.8 g, 562 mmol) in water, and the obtained two-layer solution was vigorously stirred with heating under reflux for 2 days. After cooling the reaction solution to room temperature, the aqueous layer was separated, and extracted with ethyl acetate (150 mL×2). The organic layer separated earlier was diluted with ethyl acetate (350 mL), and washed with saturated aqueous sodium hydrogen carbonate solution (150 mL×2) and saturated brine (100 mL). The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL×2) and saturated brine (150 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (17.8 g, 66%) as a pale-brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturewith heating
  4. temperatureunder reflux for 2 days
  5. customthe aqueous layer was separated
  6. extractionextracted with ethyl acetate (150 mL×2)
  7. customThe organic layer separated earlier
  8. additionwas diluted with ethyl acetate (350 mL)
  9. washwashed with saturated aqueous sodium hydrogen carbonate solution (150 mL×2) and saturated brine (100 mL)
  10. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL×2) and saturated brine (150 mL)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationThe insoluble material was filtered off
  13. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b618f730c0f2486b993da917401a1595
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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