Water → HCID 178517481, compound

HRID 2389805Notes

Reaction equation

HRID 2389805 reaction equation
[C:1]([CH:3]=[C:4]([NH:13][C:14](=O)[O:15]CC)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])#[N:2].[F:19][C:20]([F:26])([F:25])[C:21]([NH:23][NH2:24])=O.O.C(OCC)(=O)C>CN1C(=O)CCC1>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:4]1[N:13]=[C:14]([OH:15])[N:24]2[N:23]=[C:21]([C:20]([F:26])([F:25])[F:19])[N:2]=[C:1]2[CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 229753TrifluoroacetohydrazideHCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

Product 1

HCID 178517481HCID 178517481, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2.10 g (7.4 mmol) of ethyl [2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate (Example 128A) and 0.95 g (7.4 mmol) of 2,2,2-trifluoroacetohydrazide are dissolved in NMP (10 ml) under argon and stirred in a flask with a calcium chloride drying tube at an oil-bath temperature of 160° C. for 4 h. The reaction mixture is cooled to RT, and water (20 ml) is added. Ethyl acetate (150 ml) and water (100 ml) are added, and the organic phase is separated off, dried with magnesium sulphate and concentrated. The residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 4:1 to 1:1). 0.97 g (38% of theory) of the product is obtained.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. customthe organic phase is separated off
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 4:1 to 1:1)
  6. custom0.97 g (38% of theory) of the product is obtained

Sources & evidence

ORD record
ord-32beb88717334268b8e41c498ab6cf96
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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