Triphenylcarbinol → N-Triphenylmethyl-4-chloro-2-trifluoroacetylaniline

HRID 582915Notes

Reaction equation

HRID 582915 reaction equation
O.Cl.[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=1.C1CCCCC1.[OH-].[Na+].[C:25](O)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC1C=CC(S(O)(=O)=O)=CC=1.O.CC(OC)(C)C>[C:26]1([C:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:8][C:7]2[CH:9]=[CH:10][C:4]([Cl:3])=[CH:5][C:6]=2[C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 6457TriphenylcarbinolHCID 8078CyclohexaneHCID 14798Sodium HydroxideHCID 441819891-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one--hydrogen chloride--water (1/1/1)

Product 1

HCID 15363080N-Triphenylmethyl-4-chloro-2-trifluoroacetylanilineYield 89.3%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate (84.4 g, 304 mmol), cyclohexane (350 mL), MTBE (95 mL), and water (100 mL) were stirred at room temperature. The resulting slurry was neutralized with 30 mL 10 N NaOH. To the organic phase was added trityl alcohol (91.0 g, 350 mmol) and TsOH (0.36 g, 1.9 mmol). The mixture was heated to reflux and 300 mL of solvent was distilled. Acetonitrile (350 mL) and diisopropylethyl amine (0.5 mL) were added and the distillation continued to remove 220 mL additional solvent. The solution was cooled in an ice bath and the product filtered to give 126.5 g (89%) of product with the same spectral and physical properties as the sample prepared in Method A.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. distillation300 mL of solvent was distilled
  4. additionAcetonitrile (350 mL) and diisopropylethyl amine (0.5 mL) were added
  5. distillationthe distillation
  6. customto remove 220 mL additional solvent
  7. temperatureThe solution was cooled in an ice bath
  8. filtrationthe product filtered

Sources & evidence

ORD record
ord-ca8ca445f0cf428a87ba5a7333f83b18
Source dataset
uspto-grants-1999_07
Patent number
US05925789

Reaction notes

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