Ammonia → HCID 58495667, compound

HRID 1190963Notes

Reaction equation

HRID 1190963 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH2:5][CH:4]([S:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:3]1.N>[Ni].C(O)C>[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH2:5][CH:4]([S:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58495561HCID 58495561, compound

Product 1

HCID 58495667HCID 58495667, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of Raney Nickel (0.2 g, 50% in water) in ethanol (35 mL) add a solution of 4-[(3,3-dimethylcyclohexyl)-thio]-benzonitrile (0.35 g, 1.43 mmol) in ethanol (5 mL) followed by aqueous ammonia (0.88 M, 2 mL) and hydrogenate the mixture in a Parr shaker at 60 psi for 3 h. Filter the mixture through Celite® washing the filter cake with ethanol. Remove the solvent in vacuo to obtain the title compound as a pale yellow oil (0.24 g, 67%).

Workup

  1. customfor 3 h
  2. filtrationFilter the mixture through Celite®
  3. washwashing the filter cake with ethanol
  4. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-d9f9621405a84f5a8f48e7611aacc814
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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