4-(3,5-Bis-trifluoromethyl-benzyl)-2-methylaniline → Phthalamide

HRID 1640094Notes

Reaction equation

HRID 1640094 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[N:12][C@@H](C)CSC)[O:5][C:6]2=[O:11].FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CC1C=CC([NH2:28])=C(C)C=1>C(#N)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:6]([NH2:28])(=[O:11])[C:7]1[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=1)[C:4]([NH2:12])=[O:5]

Participants

5

Reactant 2

HCID 120027444-(3,5-Bis-trifluoromethyl-benzyl)-2-methylanilineHCID 57450847HCID 57450847, compound

Product 1

HCID 6956PhthalamideYield 92.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6342AcetonitrileSolvent

Procedure

4-Chloro-3-[(S)-1-methyl-2-methylthioethylimino]-3-H-isobenzofuran-1-one (0.2 g) and 4-(3,5-bis-trifluoromethyl-benzyl)-2-methylaniline (0.22 g) were dissolved in acetonitrile (10 ml), to which p-toluenesulfonic acid hydrate (0.01 g) was added, and then stirred at room temperature for three hours. After the reaction, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain N1-[4-(3,5-bis-trifluoromethyl-benzyl)-2-methylphenyl]-3-chloro-N2-(S)-1-methyl-2-methylthioethyl)phthalamide (0.10 g).

Workup

  1. additionwas added
  2. customAfter the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-60c32869c3ba4c569d311b7cd3b80996
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Reaction notes

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