HCID 13478030, compound → HCID 13478031, compound

HRID 371509Notes

Reaction equation

HRID 371509 reaction equation
[N:1]([CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)=[O:6])=[N+]=[N-].[H][H]>[Ni].O1CCOCC1.C(O)C>[NH2:1][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)(=[O:16])=[O:15])=[CH:12][CH:13]=1)=[O:6]

Participants

6

Reactant 2

HCID 13478030HCID 13478030, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13478031HCID 13478031, compoundYield 55.8%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 12 g of 2-azido-4'-(m-chlorophenylsulfonyl)acetanilide and 8 ml of Raney nickel in 150 ml of p-dioxane and 50 ml of ethanol was hydrogenated in a Parr shaker with an initial pressure of 30 psi of hydrogen for 2 hours. The mixture was filtered through a celite pad and the volatiles removed from the filtrate. The residue was crystallized from p-dioxane, giving 6.2 g of the desired product, mp 195°-196° C.

Workup

  1. customfor 2 hours
  2. filtrationThe mixture was filtered through a celite pad
  3. customthe volatiles removed from the filtrate
  4. customThe residue was crystallized from p-dioxane

Sources & evidence

ORD record
ord-a74329430aa740d59cc5ccce727a6fcd
Source dataset
uspto-grants-1985_07
Patent number
US04532349

Reaction notes

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