HCID 19046449, compound → HCID 19046432, compound

HRID 1757235Notes

Reaction equation

HRID 1757235 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([CH2:12]SC)[C:8]([NH2:9])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:11]=[C:10]([CH3:12])[C:8]([NH2:9])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 19046449HCID 19046449, compound

Product 1

HCID 19046432HCID 19046432, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-t-Butyl-2-chloro-6-(methylthiomethyl)aniline (1.3 g) was dissolved in methanol (50 ml) and Raney nickel (prewashed to pH 7) was added portionwise until t.l.c. indicated all starting material had reacted (ether-hexane, 1:10). The Raney nickel was removed by filtration through celite and the filtrate was evaporated. The residue was dissolved in ether and washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using hexane--5% ether in hexane as eluant to afford the product as a yellow liquid. 1H NMR (360 MHz, CDCl3) δ1.26 (9H, s, (CH3)3), 2.19 (3H, s, CH3), 3.97 (2H, s, NH2), 6.97 (1H, d, J=2.0 Hz, ArH), 7.14 (1H, d, J=2.0 Hz, ArH).

Workup

  1. customThe Raney nickel was removed by filtration through celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified on silica

Sources & evidence

ORD record
ord-0dc1f02fd7d14e34a09343794444abe7
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

Loading…