Sodium hydride → HCID 19889042, compound

HRID 653582Notes

Reaction equation

HRID 653582 reaction equation
[H-].[Na+].[NH2:3]/[C:4](/[C:11]([F:14])([F:13])[F:12])=[CH:5]\[C:6]([O:8]CC)=O.[Cl:15][C:16]1[C:21]([C:22]2[O:23][C:24]([CH3:27])=[N:25][N:26]=2)=[CH:20][C:19]([N:28]=[C:29]=[O:30])=[C:18]([F:31])[CH:17]=1>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:15][C:16]1[C:21]([C:22]2[O:23][C:24]([CH3:27])=[N:25][N:26]=2)=[CH:20][C:19]([N:28]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[NH:3][C:29]2=[O:30])=[C:18]([F:31])[CH:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 19889040HCID 19889040, compound

Product 1

HCID 19889042HCID 19889042, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 1.04 g of sodium hydride (oil, purity: 55%) in 75 ml of dimethylformamide, a solution of 4.3 g of ethyl 3-amino-4,4,4-trifluorocrotonate in 58 ml of toluene was added dropwise at 0° C. over a period of 15 minutes. Thereafter, the solution was stirred at 0° C. for 15 minutes and then cooled to -30° C., followed by dropwise addition of a solution of 5.7 g of 4-chloro-2-fluoro-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl isocyanate in 60 ml of toluene. The resulting mixed solution was stirred at room temperature for 3 hours.

Workup

  1. temperaturecooled to -30° C.
  2. additionThe resulting mixed solution
  3. stirringwas stirred at room temperature for 3 hours

Sources & evidence

ORD record
ord-5c48e816d64e41ec8201571df2c52a5c
Source dataset
uspto-grants-1992_07
Patent number
US05127935

Reaction notes

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