Water → [4-[(4-Bromo-2-methylphenyl)ethylamino]-2-chlorophenyl](2-methylphenyl)methanone

HRID 1264198Notes

Reaction equation

HRID 1264198 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:23]=[CH:22][C:12]([C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH3:21])=[O:14])=[C:11]([Cl:24])[CH:10]=2)=[C:4]([CH3:25])[CH:3]=1.[H-].[Na+].[CH2:28](I)[CH3:29].O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:9]2[CH:23]=[CH:22][C:12]([C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH3:21])=[O:14])=[C:11]([Cl:24])[CH:10]=2)[CH2:28][CH3:29])=[C:4]([CH3:25])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10180060HCID 10180060, compound2×

Product 1

HCID 10275183[4-[(4-Bromo-2-methylphenyl)ethylamino]-2-chlorophenyl](2-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-bromo-2-methyl-phenylamino)-2-chloro-2′-methylbenzophenone (Compound 136)(110 mg) in dry tetrahydrofurane (2.0 ml was added sodium hydride (19 mg) in one portion under stirring. After 10 min at room temperature ethyl iodide (124 mg ) was added and the reaction mixture was stirred for 18 hours under reflux, then poured into water and extracted with EtOAc. The organic phases were separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography using a mixture of EtOAc/pentane 1:8 as eluant to yield the title compound as an oil.

Workup

  1. stirringthe reaction mixture was stirred for 18 hours
  2. temperatureunder reflux
  3. extractionextracted with EtOAc
  4. customThe organic phases were separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography
  9. additiona mixture of EtOAc/pentane 1:8 as eluant

Sources & evidence

ORD record
ord-829ca5a29def435d88ac3fb44dac5dbf
Source dataset
uspto-grants-2003_04
Patent number
US06541670B2

Reaction notes

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