Sodium hydride → HCID 19896208, compound

HRID 1196762Notes

Reaction equation

HRID 1196762 reaction equation
[H-].[Na+].[NH2:3][C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[CH:5][C:6]([O:8]CC)=O.[F:18][C:19]([F:34])([F:33])[O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=O)[O:29]CC)=[CH:23][CH:22]=1>CN(C)C=O>[F:18][C:19]([F:33])([F:34])[O:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[NH:3][C:28]2=[O:29])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19896215Ethyl [4-(trifluoromethoxy)phenyl]carbamateHCID 67836558HCID 67836558, compound

Product 1

HCID 19896208HCID 19896208, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g of sodium hydride (purity: 55%) was added to 100 ml of dimethylformamide, followed by dropwise addition of 7.9 g of ethyl 3-amino-3-(2-chlorophenyl)-2-propenoate to the solution with stirring at 0° C. The resulting solution was stirred at room temperature for 15 minutes and added with 8.7 g of ethyl 4-trifluoromethoxyphenylcarbamate. The solution was further stirred at 100° C. for 4 hours. Then the solvent was distilled away under reduced pressure and the residue was dissolved in 200 ml of water and washed twice with diethyl ether. This aqueous solution was added to a mixed solution of 100 g of ice and 50 ml of concentrated hydrochloric acid. The precipitated crystals were filtered out and dried under reduced pressure to obtain 10.7 g of a crude product. This crude product was washed with heated diisopropyl ether and dried to obtain 9.7 g of the objective compound.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 15 minutes
  2. stirringThe solution was further stirred at 100° C. for 4 hours
  3. distillationThen the solvent was distilled away under reduced pressure
  4. dissolutionthe residue was dissolved in 200 ml of water
  5. washwashed twice with diethyl ether
  6. additionThis aqueous solution was added to a mixed solution of 100 g of ice and 50 ml of concentrated hydrochloric acid
  7. filtrationThe precipitated crystals were filtered out
  8. customdried under reduced pressure
  9. customto obtain 10.7 g of a crude product
  10. washThis crude product was washed with heated diisopropyl ether
  11. customdried

Sources & evidence

ORD record
ord-19374522c6d54caeb96e7c2624b7ab46
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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