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

HRID 1627389Notes

Reaction equation

HRID 1627389 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-2b85d3656c494ec5a11c62e29df69b2f
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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