Methanesulfonic Acid → HCID 19073538, compound

HRID 1290229Notes

Reaction equation

HRID 1290229 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]([N:9]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10](=O)[C:11]([F:14])([F:13])[F:12])[C:7]#N)=[CH:4][CH:3]=1.[CH3:25]S(O)(=O)=O.[C:30](#[N:33])C=C>C1(C)C=CC=CC=1>[CH2:16]([N:9]1[C:10]([C:11]([F:14])([F:12])[F:13])=[CH:25][C:7]([C:30]#[N:33])=[C:6]1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][CH:23]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic Acid2×HCID 7855AcrylonitrileHCID 21217097HCID 21217097, compound

Product 1

HCID 19073538HCID 19073538, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-(p-chloro-α-cyanobenzyl)-2,2,2-trifluoro-N-benzylacetamide (10.6 g, 0.03 mol) in toluene is treated with methanesulfonic acid (3.2 g, 0.033 mol) and acrylonitrile (3.9 g, 0.045 mol), heated at 100°-105° C. for 18 hours, cooled, treated with additional methanesulfonic acid (1.6 g, 0.017 mol), heated at 100°-105° C. for 22 hours, quenched with water and extracted with ethyl acetate. The organic extracts are combined and concentrated in vacuo to give a residue. The residue is purified by flash column chromatography using silica gel packed and eluted with 15% ethyl acetate in heptane to give the title product as white crystals, 4.4 g (40.6% yield), mp 103.5°-105.5° C., identified by 1H, 13C and 19F NMR and mass spectral analyses.

Workup

  1. temperatureheated at 100°-105° C. for 18 hours
  2. temperaturecooled
  3. temperatureheated at 100°-105° C. for 22 hours
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue is purified by flash column chromatography
  9. washeluted with 15% ethyl acetate in heptane

Sources & evidence

ORD record
ord-571ea452d83446398d22d33f4a9ea024
Source dataset
uspto-grants-1998_05
Patent number
US05750726

Reaction notes

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