3-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one → HCID 86732294, compound

HRID 517173Notes

Reaction equation

HRID 517173 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[N:9]=[C:10]=[O:11])=[CH:4][CH:3]=1.[F:13][C:14]([F:30])([F:29])[C:15]1[CH:16]=[C:17]([NH:21][C:22]2[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH:23]=2)[CH:18]=[CH:19][CH:20]=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:23]3[C:24](=[O:28])[CH2:25][CH2:26][CH2:27][C:22]=3[N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:29])[F:30])[CH:16]=3)[C:10](=[O:11])[NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27486303-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-oneHCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene

Product 1

HCID 86732294HCID 86732294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (4.25 g, 17.24 mmol) in dichloromethane (30 mL) is added to a solution of 3-(3-(trifluoromethyl)phenylamino)-cyclohex-2-enone (4.00 g, 15.67 mmol) in dichloromethane (60 mL) and the resulting mixture is heated at reflux for 3 h and stirred at room temperature over night. All volatiles are evaporated and the residue is purified by flash chromatography on silica (gradient dichloromethane/methanol 100:0 to 98:2). Yield: 5.10 g; ESI mass spectrum: [(79Br)-M+H]+=465, [(81Br)-M+H]+=467; Retention time HPLC: 1.44 min (V001—006).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 3 h
  3. customAll volatiles are evaporated
  4. customthe residue is purified by flash chromatography on silica (gradient dichloromethane/methanol 100:0 to 98:2)
  5. custom1.44 min (V001—006)

Sources & evidence

ORD record
ord-5079afa8684d457aa202c7bb2a794eda
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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