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

HRID 2184187Notes

Reaction equation

HRID 2184187 reaction equation
[F:1][C:2]1[C:7](F)=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][CH2:13][OH:14].[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[C:2]([F:1])=[C:3]([CH2:12][CH2:13][OH:14])[C:4]([N+:9]([O-:11])=[O:10])=[CH:5][CH:6]=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 1,036.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2,3-difluoro-6-nitrophenyl)ethanol (6.00 g, 29.6 mmol), as prepared in the preceding step, tert-butylamine (18.6 mL, 1.77 mmol), DMSO (30 mL), and toluene (5 mL) was heated at reflux for 16 hours. After cooling to ambient temperature the brown solution was poured into H2O (300 mL), and the deposited yellow crystals were filtered and washed with H2O twice. The yellow solid was dissolved in CHCl3 (70 mL), dried over Na2SO4, concentrated, and crystallized from hexane to give the title compound (4.70 g, 62% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.92 (dd, J=9.3, 1.5 Hz, 1H), 6.79 (t, J=8.7 Hz, 1H), 4.69 (br s, 1H), 3.96 (dd, J=11.4, 5.9 Hz, 2H), 3.32 (dt, J=6.5, 3.1 Hz, 2H), 1.75 (t, J=5.3 Hz, 1 H), 1.46 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationthe deposited yellow crystals were filtered
  4. washwashed with H2O twice
  5. dissolutionThe yellow solid was dissolved in CHCl3 (70 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customcrystallized from hexane

Sources & evidence

ORD record
ord-5d271deb45824e7982bfa383ef6d290c
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

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