Hydrochloric Acid → 2-(4-Methylthiobenzyl)amino-5-fluoronitrobenzene

HRID 653675Notes

Reaction equation

HRID 653675 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][S:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+].Cl>II>[CH3:12][S:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:1][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 677694-Fluoro-2-nitroanilineHCID 701281-(Chloromethyl)-4-(methylthio)benzeneHCID 517045Sodium Acetate

Product 1

HCID 149529802-(4-Methylthiobenzyl)amino-5-fluoronitrobenzeneYield 51.3%

Reagents, catalysts & solvents 1

HCID 807IodineCatalyst

Conditions

Temperature
120 °C

Procedure

24.8 g of 2-amino-5-fluoronitrobenzene and 27.6 g of 4-methylthiobenzyl chloride are mixed and 14.4 g of anhydrous sodium acetate and 0.3 g of iodine are added. The mixture is heated at 120° C. for 12 hours, with stirring, and is then cooled, taken up with a dilute solution of hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with dilute hydrochloric acid and then with water, dried over magnesium sulfate and evaporated to dryness. The oil obtained crystallizes from isopropyl ether to give 23.8 g of 2-(4-methylthiobenzyl)amino-5-fluoronitrobenzene in the form of crystals melting at 117° C.

Workup

  1. temperatureis then cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with dilute hydrochloric acid
  4. dry with materialwith water, dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe oil obtained
  7. customcrystallizes from isopropyl ether

Sources & evidence

ORD record
ord-5e3ba0f5d3e549d9a1d8718109009076
Source dataset
uspto-grants-1992_07
Patent number
US05128359

Reaction notes

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