Water → HCID 10292435, compound

HRID 1264197Notes

Reaction equation

HRID 1264197 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[CH3:25])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[O:5].[H-].[Na+].[CH3:28]I.O>CN1CCCC1=O>[Cl:1][C:2]1[CH:16]=[C:15]([N:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[CH3:25])[CH3:28])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9798659EO 16062×

Product 1

HCID 10292435HCID 10292435, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-chloro-4-(4-fluoro-2-methyl-phenylamino)-2′-methylbenzophenone (Compound 116)(105 mg) in N-methyl-2-pyrolidinone (2.0 ml) was added sodium hydride (14 mg) in one portion under stirring. After 10 min at 0° C. methyl iodide (47 mg ) was added and the reaction mixture was stirred for 4 hours at room temperature followed by 18 hours at 100° C. The reaction mixture was 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 diethylether/pentane 1:4 as eluant to yield the title compound.

Workup

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

Sources & evidence

ORD record
ord-174d07a13f984ce9a033ec9c1214ff1d
Source dataset
uspto-grants-2003_04
Patent number
US06541670B2

Reaction notes

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