Sodium Sulfite → N-(2-t-Butyl-5-carbamoylphenyl)-3-(5-chloro-2,4-dimethoxyphenyl)octanamide

HRID 1637450Notes

Reaction equation

HRID 1637450 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[NH2:20])=[CH:15][C:14]=1[NH:22][C:23](=[O:41])[CH2:24][CH:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=1[O:39][CH3:40])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH3:12])([CH3:11])[CH3:10].S([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.C(OC(C)C)(C)C>C(#N)C.C(Cl)Cl>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[NH2:20])=[CH:15][C:14]=1[NH:22][C:23](=[O:41])[CH2:24][CH:25]([C:31]1[CH:36]=[C:35]([Cl:1])[C:34]([O:37][CH3:38])=[CH:33][C:32]=1[O:39][CH3:40])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH3:10])([CH3:11])[CH3:12]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 19348437N-(2-t-Butyl-5-carbamoylphenyl)-3-(2,4-dimethoxyphenyl)octanamideHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 19348673N-(2-t-Butyl-5-carbamoylphenyl)-3-(5-chloro-2,4-dimethoxyphenyl)octanamideYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

181 mg (1.36 mmol) of N-chlorosuccinimide were added to a solution of 504 mg (1.11 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Example 2) in a mixture of 10 ml of acetonitrile and 4 ml of methylene chloride, and the resulting mixture was stirred at 50° C. for 15 hours. At the end of this time, the reaction mixture was allowed to cool to room temperature, after which a 1M aqueous solution of sodium sulfite was added to decompose any excess of the reagent. The mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel using ethyl acetate as the eluent, to give 434 mg (yield 80%) of the title compound as crystals, melting at 161.5-163.5° C. (from ethyl acetate-isopropyl ether).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 50 g of silica gel

Sources & evidence

ORD record
ord-d649036427b04064b74c1d10d5b17327
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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