Toluene → 2-(4-Cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]thioacetimidate methyl ester

HRID 2089682Notes

Reaction equation

HRID 2089682 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][CH2:24][OH:25])[C:15]=2[F:26])[C:11]([NH2:13])=[S:12])=[CH:5][CH:4]=1)#[N:2].F[B-](F)(F)F.[CH3:32][O+](C)C.C1(C)C=CC=CC=1>C(#N)C.[O-2].[O-2].[Mn+4]>[CH3:32][S:12][C:11](=[NH:13])[C:10](=[N:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][CH2:24][OH:25])[C:15]=1[F:26]

Participants

6

Reactant 3

HCID 1140TolueneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 866774072-(4-Cyanophenylamino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]thioacetamide

Product 1

HCID 866774092-(4-Cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]thioacetimidate methyl ester

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-cyanophenylamino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxypheny l]thioacetamide (100 g, 267 mmol) in acetonitrile (600 mL), under water cooling, trimethyloxonium tetrafluoroborate (39.5 g, 267 mmol) was added over 20 minutes, and the resulting mixture was stirred at room temperature for 0.5 hours. To the solution, under water cooling, manganese dioxide (139 g, 1.602 mmol) was added over 10 minutes, and the resulting mixture was stirred at room temperature for 1 hour. Toluene (500 mL) was added to the reaction mixture, and the resulting mixture was filtered, after which the resulting filter cake was washed with ethyl acetate. The filtrate obtained and a washing solution were combined, and the resulting mixture was sequentially washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated saline, dried over anhydrous magnesium sulfate, and then filtered. The filtrate obtained was concentrated under reduced pressure to obtain a crude product of the captioned compound as an oily product.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. filtrationthe resulting mixture was filtered
  3. filtrationafter which the resulting filter cake
  4. washwas washed with ethyl acetate
  5. customThe filtrate obtained
  6. washthe resulting mixture was sequentially washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate obtained
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d435494ee1740e59598d6dfc0f976e8
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

Loading…