Acetone Cyanohydrin → HCID 22475632, compound

HRID 2184072Notes

Reaction equation

HRID 2184072 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:18][C:19]([CH3:23])([OH:22])[C:20]#[N:21]>C1COCC1.CCOC(C)=O>[OH2:17].[C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])=[O:22].[CH3:18][C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:6][CH:7]=1)([CH3:23])[C:20]#[N:21]

Participants

6

Reactant 2

HCID 6406Acetone CyanohydrinHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 2

HCID 22392675Trifluoroacetic acid waterHCID 22475632HCID 22475632, compoundYield 131.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (Oakwood, 5.0 g, 19.3 mmol) and acetone cyanohydrin (3.6 mL, 39.8 mmol) in THF (19 mL) was heated at reflux over 24 h. After cooling, the reaction mixture was diluted with EtOAc and washed several times with brine. Purification by reverse phase HPLC using a gradient elution of 60:40 H2O/TFA:CH3CN to 0:100 H2O/TFA:CH3CN at 254 nm afforded the title compound as a white powder (2.76 g, 44%). MS (ES+) m/z 327 (MH+).

Workup

  1. temperatureat reflux over 24 h
  2. temperatureAfter cooling
  3. washwashed several times with brine
  4. customPurification by reverse phase HPLC
  5. washa gradient elution of 60:40 H2O/TFA

Sources & evidence

ORD record
ord-9435d8cf899b43dea055c18983c24826
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

Loading…