Sodium hydride → HCID 19896224, compound

HRID 1196773Notes

Reaction equation

HRID 1196773 reaction equation
[NH2:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[CH:3][C:4]([O:6]CC)=O.[H-].[Na+].[F:18][C:19]([F:32])([F:31])[C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27](=O)[O:28]C)=[N:24][CH:25]=1>CN(C)C=O>[F:31][C:19]([F:18])([F:32])[C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:15])[NH:1][C:27]2=[O:28])=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53884098HCID 53884098, compoundHCID 67836558HCID 67836558, compound

Product 1

HCID 19896224HCID 19896224, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.27 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate was added dropwise to a 20 ml of dimethylformamide solution of 0.26 g of sodium hydride (purity: 55%). The solution was stirred t room temperature for 15 minutes, then cooled to 0° C. and added with 1.24 g of methyl (5-trifluoromethyl-2-pyridyl)carbamate. The resulting solution was further stirred at 120° C. for 5 hours and then the solvent was distilled away under reduced pressure. The residue was dissolved with 100 ml of water and washed with diethyl ether. The obtained aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice, and the precipitated crystals were filtered out and dried to obtain 0.21 g of the objective compound.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe resulting solution was further stirred at 120° C. for 5 hours
  3. distillationthe solvent was distilled away under reduced pressure
  4. dissolutionThe residue was dissolved with 100 ml of water
  5. washwashed with diethyl ether
  6. additionThe obtained aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice
  7. filtrationthe precipitated crystals were filtered out
  8. customdried

Sources & evidence

ORD record
ord-e8ff63c6c9eb48bbbda74cdad155ccae
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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