Ammonia → HCID 57584571, compound

HRID 388362Notes

Reaction equation

HRID 388362 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])#[N:2].N>CO.[Ni].CCO>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 58506359HCID 58506359, compound

Product 1

HCID 57584571HCID 57584571, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

N-(2-cyano-5-methyl-phenyl)-N-methyl-methanesulphonamide (B-1a) (10.0 g, 44.6 mmol) is dissolved in 60 mL MeOH and 20 mL methanolic ammonia (7 M) in a hydrogenating autoclave and combined with Raney nickel in EtOH (1 g). The reaction mixture is then hydrogenated at 3 bar H2 and 80° C. for 16 h. After the reaction has ended the reaction mixture is filtered and the filtrate is mixed with ethanolic HCl (4.5 mL, 10 M). The precipitate formed is filtered off and the solid B-2a (HPLC-MS: tRet.=1.03 min; MS (M+H)+=229) is used without any further purification.

Workup

  1. filtrationis filtered
  2. additionthe filtrate is mixed with ethanolic HCl (4.5 mL, 10 M)
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. customthe solid B-2a (HPLC-MS: tRet.=1.03 min; MS (M+H)+=229) is used without any further purification

Sources & evidence

ORD record
ord-2842c0284f9e4e468f77692e624075dc
Source dataset
uspto-grants-2013_02
Patent number
US08377943B2

Reaction notes

Loading…