Toluene → HCID 68888626, compound

HRID 1760589Notes

Reaction equation

HRID 1760589 reaction equation
C(OC(=O)/C(=N\[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[CH3:16])/C)C.[C:18]1(C)C=CC(S(O)(=O)=O)=C[CH:19]=1.[C:29](=[O:32])(O)[O-:30].[Na+].[C:34]1(C)C=CC=C[CH:35]=1>>[CH2:34]([O:30][C:29]([C:18]1[NH:8][C:9]2[C:14]([CH:19]=1)=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[CH3:16])=[O:32])[CH3:35]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 87613830HCID 87613830, compound

Product 1

HCID 68888626HCID 68888626, compoundYield 24%

Procedure

A mixture of 7.6 g (E)/(Z)-2-[(3-fluoro-2-methyl-phenyl)-hydrazono]-propionic acid ethyl ester and 8.2 g p-toluenesulfonic acid (dried by azeotropic distillation with toluene) was heated 1 h at reflux in toluene. The solution was cooled, poured into half-saturated aqueous sodium bicarbonate solution, and the aqueous phase extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel (8:1 to 6:1 hexane/ethyl acetate eluant) to afford the title compound as a light brown solid, (24% yield, mp 149° C.; EI-MS m/e: 221.1 (M+))

Workup

  1. temperaturewas heated 1 h
  2. temperatureThe solution was cooled
  3. extractionthe aqueous phase extracted twice with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (8:1 to 6:1 hexane/ethyl acetate eluant)

Sources & evidence

ORD record
ord-b981effb022d48939758b3853ccc69c5
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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