Ethanol → HCID 68709923, compound

HRID 2067937Notes

Reaction equation

HRID 2067937 reaction equation
Cl[C:2](Cl)(Cl)[C:3](=O)[CH:4]=[C:5](OCC)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH3:19][NH:20][NH2:21].Cl.[CH3:23][CH2:24][OH:25].C([OH:28])C>>[CH2:24]([O:25][C:2]([C:3]1[CH:4]=[C:5]([C:6]2[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=2)[N:20]([CH3:19])[N:21]=1)=[O:28])[CH3:23]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 6061MethylhydrazineHCID 21887872Ethanol hydrochlorideHCID 68709804HCID 68709804, compound

Product 1

HCID 68709923HCID 68709923, compound

Procedure

A solution of 10.15 g [1,1,1-Trichloro-4-ethoxy-4-(4-fluoro-phenyl)-but-3-en-2-one in 50 ml of Ethanol was added dropwise to a solution of 2.1 ml of Methylhydrazine and 4.7 ml of 9N HCl/EtOH in 250 ml of Ethanol. The reaction mixture was stirred at reflux for 2 hrs. The yellow solution was allowed to cool and concentrated in vaccuo. The residue was taken up in 200 ml of Methylene chloride. The organic phase was washed successively with 1N HCl solution and water. After drying over Magnesium sulfate and concentration, the crude product (8.56 g) was purified by chromatography over silica gel using a 2:1 mixture of Heptane and Ethyl acetate as eluant. The solvents were evaporated, and the desired compound was obtained as a yellow oil (2.79 g, 35%), which solidified on standing, MS: m/e=249.1 ([M+1]+).

Workup

  1. temperatureat reflux for 2 hrs
  2. temperatureto cool
  3. concentrationconcentrated in vaccuo
  4. washThe organic phase was washed successively with 1N HCl solution and water
  5. dry with materialAfter drying over Magnesium sulfate and concentration
  6. customthe crude product (8.56 g) was purified by chromatography over silica gel using
  7. additiona 2:1 mixture of Heptane and Ethyl acetate as eluant
  8. customThe solvents were evaporated

Sources & evidence

ORD record
ord-fa730ae871a74019b0609326c10b1b80
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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