Water → HCID 178517470, compound

HRID 2389806Notes

Reaction equation

HRID 2389806 reaction equation
[C:1]([CH:3]=[C:4]([NH:15][C:16](=[O:20])OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)#[N:2].[F:21][C:22]([F:28])([F:27])[C:23]([NH:25][NH2:26])=O.C(OCC)(=O)C.O>CN1C(=O)CCC1>[F:21][C:22]([F:28])([F:27])[C:23]1[N:2]=[C:1]2[N:26]([C:16]([OH:20])=[N:15][C:4]([C:5]3[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=3)=[CH:3]2)[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 229753TrifluoroacetohydrazideHCID 76754610Ethyl {2-cyano-1-[4-(trifluoromethyl)phenyl]ethenyl}carbamate

Product 1

HCID 178517470HCID 178517470, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2.42 g (8.5 mmol) of ethyl {2-cyano-1-[4-(trifluoromethyl)phenyl]ethenyl}carbamate (Example 129A) and 1.09 g (8.5 mmol) of 2,2,2-trifluoroacetohydrazide are dissolved in NMP (10 ml) 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 ethyl acetate (150 ml) and water (100 ml) are added. The organic phase is separated off, dried with magnesium sulphate and concentrated. The residue is stirred with diethyl ether (25 ml), and the solid is filtered off and dried. 0.67 g (23% 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. stirringThe residue is stirred with diethyl ether (25 ml)
  6. filtrationthe solid is filtered off
  7. customdried
  8. custom0.67 g (23% of theory) of the product is obtained

Sources & evidence

ORD record
ord-39287de0c7d445be8dec6a7f27255969
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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