Sodium hydride → Tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate

HRID 1156130Notes

Reaction equation

HRID 1156130 reaction equation
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:21](Cl)=[O:22]>COCCOC>[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:21]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 205364403-Fluoro-4-hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 53991576Tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 28.0 g. of tert-butyl ethyl malonate in 10 ml. of 1,2-dimethoxyethane is added to a suspension of 4.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 17.3 g. of 3-fluoro-4-(hexadecylamino)benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 5 hours, cooled, poured on ice and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to dryness. The residue is then recrystallized from ether to yield tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. washThe ether solution is washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue is then recrystallized from ether

Sources & evidence

ORD record
ord-1b79b374de5e44b2b392a19b60301671
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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