Water → HCID 178517472, compound

HRID 2389812Notes

Reaction equation

HRID 2389812 reaction equation
[C:1]([CH:3]=[C:4]([NH:15]C(=O)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].[NH:21]([C:23](=[O:27])C(O)=O)[NH2:22].O.[C:29](OCC)(=O)C>CN1C(=O)CCC1>[F:12][C:11]([F:14])([F:13])[C:8]1[CH:9]=[CH:10][C:5]([C:4]2[N:15]=[C:23]([OH:27])[N:21]3[N:22]=[CH:29][N:2]=[C:1]3[CH:3]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 222877Hydrazino(oxo)acetic acidHCID 76754610Ethyl {2-cyano-1-[4-(trifluoromethyl)phenyl]ethenyl}carbamate

Product 1

HCID 178517472HCID 178517472, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2.00 g (7.0 mmol) of ethyl [2-cyano-1-(4-trifluoromethylphenyl)ethenyl]carbamate (Example 129A) and 0.73 g (7.0 mmol) of hydrazino(oxo)acetic acid are dissolved in NMP (7 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 suspended in water in an ultrasonic bath for 10 min. and then stirred for 30 min. The solid is filtered off and dried. 0.97 g (38% 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. waitThe residue is suspended in water in an ultrasonic bath for 10 min.
  7. stirringstirred for 30 min
  8. filtrationThe solid is filtered off
  9. customdried
  10. custom0.97 g (38% of theory) of the product are obtained

Sources & evidence

ORD record
ord-ed95229fbbd6484baa71c8cee35fb1aa
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

Loading…