Water → HCID 178470153, compound

HRID 2389807

Reaction equation

HRID 2389807 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].[NH:19]([C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH2:20].C(OCC)(=O)C.O>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:20]2[N:19]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:2]=[C:1]2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2786935Ethyl 2-hydrazinyl-2-oxoacetateHCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

Product 1

HCID 178470153HCID 178470153, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

3.0 g (10.5 mmol) of ethyl [2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate (Example 128A) and 1.39 g (10.5 mmol) of ethyl hydrazino(oxo)acetate are dissolved in NMP (16 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 chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1, then with dichloromethane/methanol 100:1). The crude product is concentrated, mixed with water and stirred for 1 h. The solid is filtered off with suction and dried; 1.31 g (35% of theory) of the product are 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 10:1 to 1:1
  6. concentrationThe crude product is concentrated
  7. additionmixed with water
  8. stirringstirred for 1 h
  9. filtrationThe solid is filtered off with suction
  10. customdried
  11. custom1.31 g (35% of theory) of the product are obtained

Sources & evidence

ORD record
ord-4ca25d775f0846cb841a97b42cd5ccb8
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Linked notes

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