Acetonitrile → HCID 59564945, compound

HRID 1259314Notes

Reaction equation

HRID 1259314 reaction equation
C(#N)C.[OH:4][CH:5]([CH3:23])[CH2:6][NH:7][C:8](=[O:22])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:10].Br([O-])(=O)=O.[Na+]>O.O.[Ru](Cl)(Cl)Cl>[O:4]=[C:5]([CH3:23])[CH2:6][NH:7][C:8](=[O:22])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=1)=[O:10]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 2917089N1-(2-hydroxypropyl)-N2-(3-(trifluoromethyl)phenyl)oxalamideHCID 23668195Sodium Bromate

Product 1

HCID 59564945HCID 59564945, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolvent3×

Procedure

Acetonitrile (3.06 L) and N-(2-hydroxypropyl)-N′-[3-(trifluoromethyl)-phenyl]ethanediamide (200 g, 1 eq) were charged to a reaction vessel to give a white slurry. A slurry of ruthenium chloride hydrate (2.33 g, 0.02 eq) in water (0.21 L) was charged to the reactor. Sodium bromate (114.4 g, 1.1 eq) was dissolved in water (0.48 L) and added dropwise to the dark brown solution over 2 hours keeping the reaction temperature between 20-25° C. The reaction was then held at 20-25° C. for a further 4 hours. Water (3.4 L) was added to the mixture and the product collected by filtration. The filter cake was washed with water (0.84 L) and dried at 65° C. The title compound (177.2 g, 89.2%) was isolated as a pale grey fluffy solid.

Workup

  1. customto give a white slurry
  2. additionadded dropwise to the dark brown solution over 2 hours
  3. custombetween 20-25° C
  4. filtrationthe product collected by filtration
  5. washThe filter cake was washed with water (0.84 L)
  6. customdried at 65° C

Sources & evidence

ORD record
ord-7d0a470c7dfe4985ba1385f951d1540e
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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