Hydrochloric Acid → 2-Nitro-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenylamine

HRID 558482Notes

Reaction equation

HRID 558482 reaction equation
Cl[C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[F:16][C:17]([F:21])([F:20])[CH2:18][OH:19].[OH-].[K+].Cl>CS(C)=O.O>[N+:9]([C:5]1[CH:4]=[C:3]([C:12]([F:15])([F:14])[F:13])[C:2]([O:19][CH2:18][C:17]([F:21])([F:20])[F:16])=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 14797Potassium HydroxideHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)aniline

Product 1

HCID 223176862-Nitro-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenylamineYield 98%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Commercially available 5-chloro-2-nitro-4-trifluoromethyl-phenylamine [CAS-No. 35375-74-7] (72.2 g, 300 mmol) was dissolved in DMSO (600 mL) and 2,2,2-trifluoroethanol (270 mL) were added at 23° C., the slightly exothermic reaction was cooled with a ice bath. KOH (85%, 99.0 g, 1500 mmol) were added slowly and the dark red reaction mixture was stirred at 23° C. for 4 days. Transferred into a 3 L flask and 1500 mL H2O were added under ice bath cooling, acidified with 3 N HCl and stirred at 23° C. for 3 h, filtered off the yellow precipitate, washed with H2O and dried in air at 60° C. to give the title compound as a yellow solid (89.47 g, 98%). MS (ISN) 303.1 [M−H].

Workup

  1. customthe slightly exothermic reaction
  2. temperaturewas cooled with a ice bath
  3. customthe dark red reaction mixture
  4. temperaturecooling
  5. stirringstirred at 23° C. for 3 h
  6. filtrationfiltered off the yellow precipitate
  7. washwashed with H2O
  8. customdried in air at 60° C.

Sources & evidence

ORD record
ord-4f539fa3ae58452bb5d9498a430fd8ec
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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