Ethyl 3-amino-4,4,4-trifluorocrotonate → HCID 19023221, compound

HRID 653578Notes

Reaction equation

HRID 653578 reaction equation
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.C[O-].[Na+].C([O:18][C:19]([NH:21][C:22]1[C:23]([F:36])=[CH:24][C:25]2[O:30][CH2:29][C:28](=[O:31])[N:27]([CH2:32][C:33]#[CH:34])[C:26]=2[CH:35]=1)=O)C>CN(C)C=O>[F:36][C:23]1[C:22]([N:21]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:19]2=[O:18])=[CH:35][C:26]2[N:27]([CH2:32][C:33]#[CH:34])[C:28](=[O:31])[CH2:29][O:30][C:25]=2[CH:24]=1

Participants

5

Reactant 3

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 10942334Sodium MethoxideHCID 19889041HCID 19889041, compound

Product 1

HCID 19023221HCID 19023221, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

1.10 g of ethyl 3-amino-4,4,4-trifluorocrotonate was added to a mixture of 0.33 g of sodium methoxide and 5 ml of dimethylformamide at room temperature. After standing for 20 minutes, the mixed solution was added with 1.76 g of 6-ethoxycarbonylamino-7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazine and heated at 130° C. for 4 hours. After cooling the solution to room temperature, the solution was poured into ice water and the resultant solution was extracted twice with diethyl ether. The aqueous layer was made acidic with dilute hydrochloric acid and extracted three times with ethyl acetate. The ethyl acetate extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. After distilling off ethyl acetate, the residue was purified by column chromatography using chloroform as developing solvent to obtain 0.20 g of the objective compound as pale yellow crystals.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. extractionthe resultant solution was extracted twice with diethyl ether
  3. extractionextracted three times with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off ethyl acetate
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-462e670f67d94c63bfb55c4e9c61cf65
Source dataset
uspto-grants-1992_07
Patent number
US05127935

Reaction notes

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