Water → HCID 178517481, compound

HRID 2171543Notes

Reaction equation

HRID 2171543 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-6d26897bf9ba4dfca33cb1ca490449c7
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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