Potassium Cyanide → N'-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide

HRID 83907Notes

Reaction equation

HRID 83907 reaction equation
[C-]#N.[K+].C([O:7][CH2:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([S:16](=[O:23])(=[O:22])[N:17]=[CH:18][N:19]([CH3:21])[CH3:20])=[CH:11][C:10]=1[Cl:24])(=O)C>CO>[Cl:24][C:10]1[CH:11]=[C:12]([S:16]([N:17]=[CH:18][N:19]([CH3:21])[CH3:20])(=[O:22])=[O:23])[CH:13]=[C:14]([F:15])[C:9]=1[CH2:8][OH:7]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 667410382-chloro-4-(N-((dimethylamino)methylene)sulfamoyl)-6-fluorobenzyl acetate

Product 1

HCID 66739970N'-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamideYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of KCN (82 mg, 1.26 mmol) in MeOH (80 mL) was added 2-chloro-4-(N-((dimethylamino)methylene)sulfamoyl)-6-fluorobenzyl acetate (850 mg, 2.52 mmol) at 0° C. The mixture was allowed to attain room temperature and then refluxed 1 h. After cooling, the reaction mixture was quenched with H2O, concentrated, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhyd MgSO4, filtered and concentrated under reduced pressure to give N′-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide (600 mg, 80%) as ivory solid. 1H NMR (400 MHz, CDCl3) δ 8.10(s, 1H), 7.74 (s, 1H), 7.55 (d, 1H), 4.86 (d, 2H), 3.17 (s, 3H), 3.05 (s, 3H), 2.07 (s, 1H).

Workup

  1. customto attain room temperature
  2. temperaturerefluxed 1 h
  3. temperatureAfter cooling
  4. customthe reaction mixture was quenched with H2O
  5. concentrationconcentrated
  6. extractionextracted with EtOAc
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over anhyd MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00fa5ab99e01439280a7a645adb6272a
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…