Sodium ethoxide → HCID 15456798, compound

HRID 1978977Notes

Reaction equation

HRID 1978977 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:8]([C:9]([O:11]C)=O)=[CH:7][N:6]=[CH:5][CH:4]=1.[C:15](=[N:20]O)([NH2:19])[CH:16]([CH3:18])[CH3:17].[O-]CC.[Na+]>C(O)C>[CH:16]([C:15]1[N:20]=[C:9]([C:8]2[CH:7]=[N:6][CH:5]=[CH:4][C:3]=2[C:2]([F:1])([F:14])[F:13])[O:11][N:19]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 2775680Methyl 4-(trifluoromethyl)nicotinateHCID 2794833N'-Hydroxy-2-methylpropanimidamide

Product 1

HCID 15456798HCID 15456798, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.

Workup

  1. temperatureto warm to room temperature over a period of two hours
  2. customwas then continued at this temperature until the reaction
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with diethyl ether
  5. customChromatographic purification of the crude product

Sources & evidence

ORD record
ord-745549145f9243fbb5a119d4d03980ff
Source dataset
uspto-grants-2001_05
Patent number
US06239160B1

Reaction notes

Loading…