HCID 19046449, compound → HCID 19046432, compound

HRID 1439936Notes

Reaction equation

HRID 1439936 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 flitrate 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) δ 1.26 (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 flitrate 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-0cf5db6318194e4a8092e8b906c1509b
Source dataset
uspto-grants-1996_03
Patent number
US05496833

Reaction notes

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