HCID 17937536, compound → HCID 69588140, compound

HRID 1791120Notes

Reaction equation

HRID 1791120 reaction equation
[C:1]([C:4](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[Cl:17])[C:5]([O:7][CH3:8])=[O:6])(=[O:3])[CH3:2].[Cl-].[CH2:19]=[N+:20]1[CH2:24][CH2:23][S:22][CH2:21]1>C(#N)C>[Cl:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[CH:9]=[C:4]([C:1](=[O:3])[CH2:2][CH2:19][N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 17937536HCID 17937536, compoundHCID 57252060Methyl 2-[(2-chloro-4-fluorophenyl)methylene]-3-oxobutanoate

Product 1

HCID 69588140HCID 69588140, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.24 g (12.6 mmol) of methyl 2-acetyl-3-(2-chloro-4-fluorophenyl)acrylate from Example VII are stirred with 1.74 g (12.6 mmol) of 3-methylene-1,3-thiazolidin-3-ium chloride [prepared in analogy to H. Mohrle et al., Z. Naturforsch. 42, 1035–1046 (1987)] in 50 ml of acetonitrile at 40° C. for 48 hours. After concentration, the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over sodium sulfate and concentrated, and the residue is chromatographed on silica gel with cyclohexane/ethyl acetate (5:1→2:1) as mobile phase.

Workup

  1. concentrationAfter concentration
  2. washwashed with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel with cyclohexane/ethyl acetate (5:1→2:1) as mobile phase

Sources & evidence

ORD record
ord-0778915747554df0b33f837117a41077
Source dataset
uspto-grants-2006_07
Patent number
US07074784B2

Reaction notes

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