HCID 22902325, compound → HCID 22902365, compound

HRID 1078360Notes

Reaction equation

HRID 1078360 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:20][N:19]=2)[CH3:13])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:20][N:19]=2)[CH3:13])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 22902325HCID 22902325, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22902365HCID 22902365, compoundYield 56.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

2.1 g of 3-(3-[N-(2-(4-nitrophenyl)-ethyl)-N-methylamino]-propyloxy)-5-phenyl-1,2,4-thiadiazole (for) preparation, see Example 8)), were dissolved in a mixture of 75 ml ethanol and 75 ml methanol and reacted with a catalytic quantity of Raney nickel. The reaction mixture was then hydrogenated for 2.5 hours at room temperature with hydrogen at a hydrogen pressure of 5 bars. The catalyst was filtered off and the filtrate concentrated to dryness. The oily crude title compound obtained was purified by medium-pressure chromatography over fine-grained silica gel (Lichroprep Si 60®) using 95:5 ethyl acetate/methanol as the eluent. 1.1 g of the title compound were obtained as an oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated to dryness
  3. customThe oily crude title compound obtained
  4. customwas purified by medium-pressure chromatography over fine-grained silica gel (Lichroprep Si 60®)

Sources & evidence

ORD record
ord-e44059025aa8415e924a50359a67e5cb
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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