Ethanol → HCID 18964271, compound

HRID 2227033Notes

Reaction equation

HRID 2227033 reaction equation
[H-].[Na+].C(O[C:6](=[O:30])[CH:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[N:8]([C:10](=[O:21])[CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])[CH3:9])C.C(O)C.[H][H]>C1(C)C=CC=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH:7]2[N:8]([CH3:9])[C:10](=[O:21])[CH:11]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:6]2=[O:30])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 15682131HCID 15682131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18964271HCID 18964271, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a boiling solution of 120 ml of absolute toluene and 7.5 g (0.25 mol) of sodium hydride there are added dropwise 79.9 g (0.199 mol) of 2-(4-chlorobenzyl)-N-(2,4,6-trimethylphenylacetyl)-sarcosine ethyl ester in 200 ml of absolute toluene, and the batch is refluxed while being monitored by thin-layer chromatography. When the reaction is complete, ethanol is added dropwise, while cooling in an ice-bath, until no more hydrogen escapes. After the mixture has been evaporated under reduced pressure, the residue is taken up in water and the mixture is acidified with concentrated hydrochloric acid at 0° C. to 20° C. The precipitate is filtered off with suction and recrystallised from chloroform/n-hexane. 48.4 g (68.4% of Theory) of 5-(4-chlorobenzyl)-1-methyl-3-(2,4,6-trimethylphenyl)-pyrrolidine-2,4-dione of melting point >230° C. are obtained.

Workup

  1. temperaturethe batch is refluxed
  2. customAfter the mixture has been evaporated under reduced pressure
  3. customis acidified with concentrated hydrochloric acid at 0° C. to 20° C
  4. filtrationThe precipitate is filtered off with suction
  5. customrecrystallised from chloroform/n-hexane

Sources & evidence

ORD record
ord-5dd289a7ece64209b1e5d0546f3b2a51
Source dataset
uspto-grants-1994_09
Patent number
US05350861

Reaction notes

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