Dimethyl Sulfoxide → 4-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene

HRID 1609061Notes

Reaction equation

HRID 1609061 reaction equation
[F:1][C:2]1[C:3]([CH2:12][CH2:13][OH:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].CS(C)=O.C1(C)C=CC=CC=1>O>[C:15]([NH:19][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[C:3]([CH2:12][CH2:13][OH:14])[C:2]=1[F:1])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 6385Tert-ButylamineHCID 224753203,4-Difluoro-2-(2-hydroxyethyl)nitrobenzene

Product 1

HCID 224753164-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30.5 g (150 mmol) of 3,4-difluoro-2-(2-hydroxyethyl)nitrobenzene and 90 ml (900 mmol) of t-butylamine were added to 150 ml of dimethylsulfoxide and 25 ml of toluene, and the solution was heated at reflux for 8.5 hours. After air-cooling, the solution was poured into 1500 ml of water, and the deposited crystals were filtered. They were dissolved in 500 ml of chloroform, and after drying over magnesium sulfate, the solvent was removed by distillation. The residue was crystallized with n-hexane, and the crystals were filtered off to obtain 35.5 g of the subject compound (123) in a 93% yield.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 8.5 hours
  3. temperatureAfter air-cooling
  4. filtrationthe deposited crystals were filtered
  5. dissolutionThey were dissolved in 500 ml of chloroform
  6. dry with materialafter drying over magnesium sulfate
  7. customthe solvent was removed by distillation
  8. customThe residue was crystallized with n-hexane
  9. filtrationthe crystals were filtered off

Sources & evidence

ORD record
ord-8995fcbc5b614fc2a92644357aa86fca
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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