4-Methyloxybenzyl chloride → Diethyl [(2,3,4-trifluoroanilino)(p-methoxybenzylthio)methylene]malonate

HRID 1382741Notes

Reaction equation

HRID 1382741 reaction equation
[Na].[F:2][C:3]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:4]=1[NH:5][C:6](=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[SH:7].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>CN(C)C=O>[F:2][C:3]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:4]=1[NH:5][C:6](=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[S:7][CH2:31][C:30]1[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 178472269HCID 178472269, compound

Product 1

HCID 14673304Diethyl [(2,3,4-trifluoroanilino)(p-methoxybenzylthio)methylene]malonateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethyl [(2,3,4-trifluoroanilino)(mercapto)methylene]malonate sodium salt (68.5 g) was dissolved in N,N-dimethylformamide (200 ml) and thereto p-methoxybenzyl chloride (28.9 g) was added dropwise at 3° to 5° C. over a period of 5 minutes. After the reaction mixture was stirred at room temperature for 1 hour and evaporated to dryness under reduced pressure, water was added to the residue and the mixture was extracted with chloroform. After the extract was washed with a NaCl solution and dried over magnesium sulfate, the solvent was distilled off under reduced pressure to give the title compound (82.9 g) as colorless solid, which was then recrystallized from a mixed solvent of haxane - benzene.

Workup

  1. customevaporated to dryness under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washAfter the extract was washed with a NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dcd2e76509234704b4c9bc066d48fab0
Source dataset
uspto-grants-1989_02
Patent number
US04808584

Reaction notes

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