Water → HCID 68760855, compound

HRID 494389

Reaction equation

HRID 494389 reaction equation
[H-].[Na+].[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Cl[C:16]1[CH:17]=[CH:18][C:19]([N+:27]([O-:29])=[O:28])=[C:20]([CH:26]=1)[C:21]([N:23]([CH3:25])[CH3:24])=[O:22].O>CN(C)C=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:16]1[CH:17]=[CH:18][C:19]([N+:27]([O-:29])=[O:28])=[C:20]([C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[CH:26]=1)[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2733872tert-Butyl methyl malonateHCID 229348075-Chloro-N,N-dimethyl-2-nitrobenzamide

Product 1

HCID 68760855HCID 68760855, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (350 mg) was dissolved in dimethylformamide (10 mL)), and the solution was cooled to 0° C. After addition of tert-butyl methyl malonate (1.52 g), the mixture was stirred for one hour, and the 5-chloro-N,N-dimethyl-2-nitrobenzamide (1.0 g) obtained in Example 2a) was added thereto. The mixture was stirred at 70° C. for 4.5 hours and water was added thereto. The resulting solution was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and purified by column chromatography on silica gel with ethyl acetate:hexane=1:1 to give the title compound (1.29 g).

Workup

  1. stirringThe mixture was stirred at 70° C. for 4.5 hours
  2. concentrationThe resulting solution was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. custompurified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-e35f076fe60b47d98db6c6cc01f6b664
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Linked notes

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