Water → HCID 178517485, compound

HRID 2389811Notes

Reaction equation

HRID 2389811 reaction equation
[C:1]([CH:3]=[C:4]([NH:13]C(=O)OCC)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])#[N:2].[NH:19]([C:21](=[O:25])C(O)=O)[NH2:20].O.[C:27](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:21]([OH:25])[N:19]2[N:20]=[CH:27][N:2]=[C:1]2[CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 222877Hydrazino(oxo)acetic acidHCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

Product 1

HCID 178517485HCID 178517485, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

500 mg (1.75 mmol) of ethyl [2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate (Example 128A) and 182 mg (1.75 mmol) of hydrazino(oxo)acetic acid are dissolved in NMP (2 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, mixed with water (20 ml) and stirred for 20 min. 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 stirred with diethyl ether/dichloromethane, and the solid is filtered off and dried. 150 mg (31% of theory) of the product are obtained.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. stirringstirred for 20 min
  3. customthe organic phase is separated off
  4. dry with materialdried with magnesium sulphate
  5. concentrationconcentrated
  6. stirringThe residue is stirred with diethyl ether/dichloromethane
  7. filtrationthe solid is filtered off
  8. customdried
  9. custom150 mg (31% of theory) of the product are obtained

Sources & evidence

ORD record
ord-78759e48ac7d4068a0dd9fe4ce45ea7d
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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