Sodium hydride → HCID 19896189, compound

HRID 1196775Notes

Reaction equation

HRID 1196775 reaction equation
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.[H-].[Na+].[F:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[CH:18][C:17]=1[NH:24][C:25](=O)[O:26]CC>CN(C)C=O>[F:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[CH:18][C:17]=1[N:24]1[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:25]1=[O:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 19896223HCID 19896223, compound

Product 1

HCID 19896189HCID 19896189, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.28 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added to a 10 ml dimethylformamide solution of 0.33 g of sodium hydride (purity: 55%) under ice cooling and stirred at room temperature for 15 minutes, followed by addition of 1.31 g of ethyl 2,3,4-trifluorophenylcarbamate and was stirred at 90° C. for 4 hours. Then dimethylformamide was distilled away under reduced pressure and the residue was dissolved in 100 ml of water. This aqueous solution was washed with diethyl ether, then added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed with water and dried, and then the solvent was distilled away under reduced pressure to obtain 0.3 g of the objective compound.

Workup

  1. stirringwas stirred at 90° C. for 4 hours
  2. distillationThen dimethylformamide was distilled away under reduced pressure
  3. dissolutionthe residue was dissolved in 100 ml of water
  4. washThis aqueous solution was washed with diethyl ether
  5. additionadded to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe obtained organic layer was washed with water
  8. customdried
  9. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-d0ba2df4091f44f7b5d5b387a77bd171
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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