Trifluoromethanesulfonic anhydride → [4-[2-[Bis-(isopropyl)-amino]-2-oxoethoxy]-2,3-dicyanophenyl]trifluoromethanesulfonate

HRID 400248Notes

Reaction equation

HRID 400248 reaction equation
C(N(C(C)C)C(C)C)C.[F:10][C:11]([F:24])([F:23])[S:12]([O:15]S(C(F)(F)F)(=O)=O)(=[O:14])=[O:13].[CH:25]([N:28]([CH:44]([CH3:46])[CH3:45])[C:29](=[O:43])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35](O)=[C:34]([C:39]#[N:40])[C:33]=1[C:41]#[N:42])([CH3:27])[CH3:26]>C(#N)C>[CH:44]([N:28]([CH:25]([CH3:27])[CH3:26])[C:29](=[O:43])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([O:15][S:12]([C:11]([F:24])([F:23])[F:10])(=[O:14])=[O:13])=[C:34]([C:39]#[N:40])[C:33]=1[C:41]#[N:42])([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 21841501N,N-bis-(isopropyl)-2-(2,3-dicyano-4-hydroxy-phenoxy)-acetamide

Product 1

HCID 21841500[4-[2-[Bis-(isopropyl)-amino]-2-oxoethoxy]-2,3-dicyanophenyl]trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.58 ml of ethyl diisopropylamine and 0.59 ml of trifluoromethanesulfonic anhydride were added to a solution of 900 mg of the product of Stage A in 50 ml of acetonitrile and the reaction medium was refluxed for one hour. Then, the solvent was evaporated under reduced pressure and the crude product obtained was chromatographed on silica, eluting with a cyclohexane-ethyl acetate mixture (50-50) to obtain 600 mg of the expected product.

Workup

  1. temperaturethe reaction medium was refluxed for one hour
  2. customThen, the solvent was evaporated under reduced pressure
  3. customthe crude product obtained
  4. customwas chromatographed on silica
  5. washeluting with a cyclohexane-ethyl acetate mixture (50-50)

Sources & evidence

ORD record
ord-c3fac434a22744048a6562508ca1523d
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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