Ammonium Hydroxide → HCID 10594392, compound

HRID 1978291Notes

Reaction equation

HRID 1978291 reaction equation
[NH4+].[OH-].[C:3]([CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:22][CH2:23][CH2:24][C:25]#[N:26])[S:10]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])(=[O:12])=[O:11])#[N:4]>[Ni].CO.C1COCC1>[C:14]1([CH3:21])[CH:15]=[C:16]([CH3:20])[CH:17]=[C:18]([CH3:19])[C:13]=1[S:10]([N:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:3][NH2:4])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])(=[O:11])=[O:12]

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 10593786HCID 10593786, compound

Product 1

HCID 10594392HCID 10594392, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Raney nickel (W-2 grade, 7.60 g) and concentrated NH4OH (10 mL) were successively added to 38 (5.06 g, 14.6 mmol) in CH3OH (30 mL) and THF (30 mL) in a 200 mL Parr bottle, and a slow stream of NH3 was bubbled through the mixture for 30 minutes at 0° C. After hydrogenation in a Parr bottle was carried out at 50-55 psi for 8 hours, the suspension was filtered through Celite, and the solvents were removed in vacuo to give 4.70 g (91%) of 41 as an oil: NMR δ 1.14-1.24 (m, 10 H), 2.25 (s, 3 H), 2.6 (s, 6 H), 3.05-3.25 (m, 8 H), 3.45 (s, 4 H), 6.9 (s, 2 H).

Workup

  1. customa slow stream of NH3 was bubbled through the mixture for 30 minutes at 0° C
  2. filtrationthe suspension was filtered through Celite
  3. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-c66af4ea8679435da15660b70357c768
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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