Water → HCID 68517643, compound

HRID 1717334Notes

Reaction equation

HRID 1717334 reaction equation
[C-:1]#[N:2].[Na+].FC(F)(F)C(O)=O.Br[CH2:12][C:13]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].O>CS(C)=O>[C:1]([CH2:12][C:13]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8929Sodium CyanideHCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Product 1

HCID 68517643HCID 68517643, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium cyanide (6.3 g) in DMSO (200 ml) was added trifluoroacetic acid (6.6 ml) under water-cooling, methyl 2-(bromomethyl)-4-nitrobenzoate (J. Med. Chem., 42, 3510-3519 (1999)) (11.8 g) synthesized separately was added, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (ethyl acetate/hexane=1/10 to 1/3) to give a crude product of the title compound as a pale-yellow powder (2.52 g, 27%). The obtained crude product was used for the next reaction without further purification.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column (ethyl acetate/hexane=1/10 to 1/3)

Sources & evidence

ORD record
ord-2cf43bf27bb54fd399b18e1fc168c1a9
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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