Benzophenone → 4-[(Diphenylmethylidene)amino]-3-methyl-2-(trifluoromethyl)benzonitrile

HRID 2101992Notes

Reaction equation

HRID 2101992 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH3:14].[C:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:16]1([C:15](=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:11])([F:12])[F:13])[C:3]=2[CH3:14])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 218752104-Amino-3-methyl-2-(trifluoromethyl)benzonitrile

Product 1

HCID 866206794-[(Diphenylmethylidene)amino]-3-methyl-2-(trifluoromethyl)benzonitrileYield 79.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 4-amino-3-methyl-2-(trifluoromethyl)benzonitrile (3.59 g, 17.9 mmol) in toluene (80 mL) was added benzophenone (3.59 g, 19.7 mmol) followed by PTSA monohydrate (0.035 g, 0.18 mmol). The reaction flask was fitted with a Dean-Stark trap and heated at reflux for 7 d. The reaction was concentrated and purified by SiO2 chromatography (5% EtOAc in hexanes) to afford 4-[(diphenylmethylidene)amino]-3-methyl-2-(trifluoromethyl)benzonitrile (5.16 g, 79%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6): δ 7.71-7.01 (m, 10H), 7.65 (d, J=8.4 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 2.30 (s, 3H).

Workup

  1. customThe reaction flask was fitted with a Dean-Stark trap
  2. temperatureheated
  3. temperatureat reflux for 7 d
  4. concentrationThe reaction was concentrated
  5. custompurified by SiO2 chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-354cf1609d80483e92b33255a6097706
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…