Toluene → N-(3,5-bis(trifluoromethyl)benzylidene)(2-chloro-5-(trifluoromethyl)phenyl)methanamine

HRID 390756

Reaction equation

HRID 390756 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=1[CH2:11][NH2:12].[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH:26]=O.C1(C)C=CC(S(N)(=O)=O)=CC=1>O>[F:21][C:22]([F:35])([F:36])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:30]=1)[CH:26]=[N:12][CH2:11][C:10]1[CH:13]=[C:14]([C:17]([F:18])([F:19])[F:20])[CH:15]=[CH:16][C:9]=1[Cl:8]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6269P-ToluenesulfonamideHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 27366822-Chloro-5-(trifluoromethyl)benzylamine

Product 1

HCID 86614963N-(3,5-bis(trifluoromethyl)benzylidene)(2-chloro-5-(trifluoromethyl)phenyl)methanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round bottom flask, equipped with a Dean Start Trap was charged 50 mL of toluene, 5.0 gm of 2-chloro-5-trifluoromethyl benzyl amine and 5.8 gm of 3,5-bis(trifluoromethyl)benzaldehyde and 50 mg of para-toluenesulfonamide. The reaction was heated until water no longer distilled off about 3 hours, then cooled to ambient temperature and the solvent removed in vacuum. The crude product was used directly in the next step without further purification. 10.0 gm.

Workup

  1. customTo a 100 mL round bottom flask, equipped with a Dean Start Trap
  2. distillationno longer distilled off about 3 hours
  3. customthe solvent removed in vacuum
  4. customThe crude product was used directly in the next step without further purification

Sources & evidence

ORD record
ord-52125c224296419883ebfc494951e33d
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Linked notes

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