p-Toluenesulfonic acid → N-(4-Methoxybenzyl)-4-chloro-2-(trifluoroacetyl)aniline

HRID 582910Notes

Reaction equation

HRID 582910 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.[OH-].[Na+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]O)=[CH:23][CH:22]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.O.C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][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:23][CH:22]=1

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 77384-Methoxybenzyl alcoholHCID 14798Sodium HydroxideHCID 441819891-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one--hydrogen chloride--water (1/1/1)

Product 1

HCID 11089189N-(4-Methoxybenzyl)-4-chloro-2-(trifluoroacetyl)aniline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 22272177Toluene waterSolvent

Procedure

To a slurry of 4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate (40.0 kg, 144 mol) in toluene (140 kg) and water (50 L) was added 30% NaOH (18 kg) to pH 7.0. After removing the aqueous phase, 4-methoxybenzyl alcohol (20 kg, 144 mol) and TsOH (1.0 kg, 5.3 mol) were added. The solution was heated to reflux and the water/toluene azeotrope (30 L) distilled. The solution was cooled to room temperature and washed with saturated brine (80 kg).

Workup

  1. additionwere added
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. distillationdistilled
  5. washwashed with saturated brine (80 kg)

Sources & evidence

ORD record
ord-53e2aeaf45e64eed9bccc53778c8ab99
Source dataset
uspto-grants-1999_07
Patent number
US05925789

Reaction notes

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