N,N-Dimethylaniline → HCID 58499548, compound

HRID 910272Notes

Reaction equation

HRID 910272 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C1(N(C)C)C=CC=CC=1.C([O:21][CH2:22][C@@H:23]([NH:39][S:40]([C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([Cl:50])[CH:44]=1)(=[O:42])=[O:41])[C:24]1[N:28]([CH2:29][CH3:30])[C:27]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[N:26][N:25]=1)C1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl>[Cl:50][C:45]1[CH:44]=[C:43]([S:40]([NH:39][C@@H:23]([C:24]2[N:28]([CH2:29][CH3:30])[C:27]([O:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[N:26][N:25]=2)[CH2:22][OH:21])(=[O:41])=[O:42])[CH:48]=[CH:47][C:46]=1[Cl:49]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 58499692HCID 58499692, compound

Product 1

HCID 58499548HCID 58499548, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

AlCl3 (49 mg) and PhNMe2 (148 mg) were added to a solution of the compound (69 mg) of Example 23 in CH2Cl2 (2.0 ml), and the mixture was stirred at room temperature for one hour. Then, AcOEt was added, and the mixture was washed with 1N hydrochloric acid and thereafter with saturated aqueous sodium chloride. The organic layer was dried (Na2SO4), filtered, and evaporated under reduced pressure to remove the solvent. Then, the resulting crude product was purified by column chromatography (OH SiO2, AcOEt/hexane=2/1) to give 54 mg of the titled compound (Compound 696) as a colorless powder.

Workup

  1. washthe mixture was washed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThen, the resulting crude product was purified by column chromatography (OH SiO2, AcOEt/hexane=2/1)

Sources & evidence

ORD record
ord-f001a18793554eaf8b4320d3becd13d5
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

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