Water → HCID 53897658, compound

HRID 1780009Notes

Reaction equation

HRID 1780009 reaction equation
[CH3:1][C:2]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=1)([CH3:7])[C:3]([CH2:5]Cl)=[O:4].[C:19]([O-:22])(=[O:21])[CH3:20].[Na+].O>CN(C=O)C>[CH3:1][C:2]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=1)([CH3:7])[C:3]([CH2:5][O:22][C:19](=[O:21])[CH3:20])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 54029353HCID 54029353, compound

Product 1

HCID 53897658HCID 53897658, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(1',1'-dimethyl-3'-chloroacetonyl)-3,5-dichlorobenzamide (20 gm, 0.065 m) was dissolved in 100 ml of dry DMF and 10.6 gm (0.128 m) of sodium acetate was added. The slurry was blanketed under a nitrogen atmosphere and then heated to 80°-90° C. for 4 days. The reaction mixture was cooled by adding 100 ml of water. The aqueous solution was extracted four times with 10 ml aliquots of methylene chloride. The combined organic extracts were washed with water (3×100 ml) and brine. The solvent was removed, the resulting white solid dried and then recrystallized from an acetone and hexane (about 1:4) mixture to yield 10.2 gm of the product.

Workup

  1. temperatureheated to 80°-90° C. for 4 days
  2. temperatureThe reaction mixture was cooled
  3. extractionThe aqueous solution was extracted four times with 10 ml aliquots of methylene chloride
  4. washThe combined organic extracts were washed with water (3×100 ml) and brine
  5. customThe solvent was removed
  6. customthe resulting white solid dried
  7. customrecrystallized from an acetone and hexane (about 1:4) mixture

Sources & evidence

ORD record
ord-4df937c9283643c487237277c7f7bbe4
Source dataset
uspto-grants-1997_05
Patent number
US05629346

Reaction notes

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