Dimethylformamide → HCID 86752404, compound

HRID 1108520Notes

Reaction equation

HRID 1108520 reaction equation
CN(C)C=O.[H-].[Na+].[C:8]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11].[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl>C1C=CC=CC=1>[C:10]([CH:9]([CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([F:17])[CH:19]=1)[C:8]([O:14][CH2:15][CH3:16])=[O:13])(=[O:11])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8868Ethyl AcetoacetateHCID 99743-Fluorobenzyl chlorideHCID 24758Sodium hydride

Product 1

HCID 86752404HCID 86752404, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 500 mL of 10% dimethylformamide in benzene was added 58.6% NaH (41 g, 1.0 mol) cooled in an ice bath was added ethyl acetoacetate (130 g, 1.0 mol) was added. The reaction was stirred at room temperature for 30 minutes, and m-fluorobenzyl chloride (145 g, 1.0 mol) was added. The reaction was heated to reflux for 3 hours and gave an NaCl precipitate which was then removed by filtration. The filtrated was poured into H2O, acidified with concentrated HCl and was extracted with a mixture of ether and benzene. The organic layer was washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by distillation (112-119° C./25 mmHg) to give compound A (133 g, 56%).

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 3 hours

Sources & evidence

ORD record
ord-09e0b2e9200b4c978a9e9a1410f0ae93
Source dataset
uspto-grants-2000_05
Patent number
US06066650

Reaction notes

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