Hydrochloric Acid → HCID 86607628, compound

HRID 1990809Notes

Reaction equation

HRID 1990809 reaction equation
[CH2:1]([OH:3])[CH3:2].[K].Cl[C:6]1[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([NH2:12])[CH:11]=1.Cl>O>[CH2:1]([O:3][NH:12][C:10]1[CH:11]=[CH:6][C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][C:9]=1[N+:13]([O-:15])=[O:14])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)anilineHCID 5462222Potassium2×

Product 1

HCID 86607628HCID 86607628, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethanol (500 mL) was added potassium metal (ca. 21 g, ca. 537 mmol, ca. 2.24 equiv) and the vigorous reaction had to be cooled with an ice bath. Stirring was continued until all potassium metal was dissolved. Solid commercially available 5-chloro-2-nitro-4-trifluoromethyl-phenylamine (57.74 g, 240 mmol, 1.0 equiv, [CAS RN 35375-74-7]) was added in one portion and the resulting dark red mixture was stirred at 55-60° C. for 4 d. The warm reaction mixture was slowly poured into water (ca. 2000 mL), the pH adjusted with a solution of 1 M HCl to 2, the yellow precipitate filtered off, washed with water and dried in air at 60° C. to give 57.81 g (96%) of the title compound as a yellow solid which was used without further purification. MS (ISN): 249.0 [M−H]−.

Workup

  1. customthe vigorous reaction
  2. temperatureto be cooled with an ice bath
  3. dissolutionwas dissolved
  4. stirringthe resulting dark red mixture was stirred at 55-60° C. for 4 d
  5. customThe warm reaction mixture
  6. filtrationthe yellow precipitate filtered off
  7. washwashed with water
  8. customdried in air at 60° C.

Sources & evidence

ORD record
ord-37d6d59ede714dd18e481b4df03920fd
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

Loading…