Sodium Acetate → HCID 21746950, compound

HRID 1034301Notes

Reaction equation

HRID 1034301 reaction equation
[C:1]([S:5][CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:25][CH:24]=2)N)=[CH:18][CH:17]=1.CC([O-])=O.[Na+]>C1(C)C=CC=CC=1.CC(O)=O>[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]2[C:23]3[C:24](=[CH:25][C:26]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:27][CH:28]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 14919330Ethyl 3-(tert-butylsulfanyl)-2-oxopropanoateHCID 19023706HCID 19023706, compound

Product 1

HCID 21746950HCID 21746950, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A solution of ethyl 3-(t-butylthio)-2-oxopropanoate (18.6 g), 1-(4-chlorobenzyl)-1-(4-allyloxyphenyl)hydrazine hydrochloride (26.3 g), and NaOAc (15 g) in 300 mL toluene and 150 mL HOAc was stirred at room temperature under nitrogen for 16 hours then at 70° C. for 2 hours. The mixture was cooled, poured onto H2O, extracted (3×) with EtOAc and, the organic layers then washed successively with sat'd. NaHCO3 and brine. After drying over MgSO4, the solution was filtered and evaporated, and the residue chromatographed (silica gel; hexane/EtOAc 4:1) to afford the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto H2O
  3. extractionextracted (3×) with EtOAc
  4. washthe organic layers then washed successively with sat'd
  5. dry with materialAfter drying over MgSO4
  6. filtrationthe solution was filtered
  7. customevaporated
  8. customthe residue chromatographed (silica gel; hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-60e9b30f41074b31bba52eb454b9e525
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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