Tetrahydrofuran → 4'-bromo-N-methyl-2'-aminobenzanilide

HRID 1172769Notes

Reaction equation

HRID 1172769 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]([CH3:15])[C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([N+:18]([O-])=O)[CH:3]=1.O1CCCC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CO>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]([CH3:15])[C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([NH2:18])[CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 230940784'-bromo-N-methyl-2'-nitrobenzanilide

Product 1

HCID 230940734'-bromo-N-methyl-2'-aminobenzanilideYield 91.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

9.5 g (28 mmol) of 4′-bromo-N-methyl-2′-nitro-benzanilide were dissolved into 100 mL of tetrahydrofuran. While the solution was stirred at room temperature in an argon atmosphere, a solution of 25 g (142 mmol) of sodium hydrosulfite in 90 mL of water was added. Furthermore, 10 mL of methanol were added, and the whole was stirred for 3 hours. Next, 100 mL of ethyl acetate were added, and then a solution of 12 g (142 mmol) of sodium hydrogen carbonate in 125 mL of water was added. After having been stirred for 1 hour, the resultant was extracted with ethyl acetate. An aqueous layer was removed, and an organic layer was washed with a 10-mass % aqueous solution of K2CO3 and a saturated sodium chloride solution, and dried with magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, with the result that 7.8 g of 4′-bromo-N-methyl-2′-amino-benzanilide were obtained as a white solid (90% yield). The coarse product was directly used for the next reaction.

Workup

  1. stirringthe whole was stirred for 3 hours
  2. stirringAfter having been stirred for 1 hour
  3. extractionthe resultant was extracted with ethyl acetate
  4. customAn aqueous layer was removed
  5. washan organic layer was washed with a 10-mass % aqueous solution of K2CO3
  6. dry with materiala saturated sodium chloride solution, and dried with magnesium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dc02277506204461b6386e687db78e7a
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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