HCID 178463249, compound → HCID 178463247, compound

HRID 1155543Notes

Reaction equation

HRID 1155543 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12](S)[NH:13][CH:14]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]>[Ni].CN(C)C=O>[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 178463249HCID 178463249, compound

Product 1

HCID 178463247HCID 178463247, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.1 g. (5 mmoles) of 4-(2-ethylamino-4-pyridyl)imidazole-2-thiol and 4.0 g. of Raney nickel in 30 ml. of dimethylformamide was heated at 120° C. for 4 hours. The catalysts was filtered through celite and the filtrate concentrated under reduced pressure to remove the solvent. The residual oil solidified on trituration with diethyl ether affording 830 mg. (88%) of the desired product. Purification by chromatographing over 35 g. of silica gel using chloroform-methanol (19:1, v:v) as the eluent gave 384 g. (41%) of pure product, m.p. 135°-137° C.

Workup

  1. additionA mixture of 1.1 g
  2. filtrationThe catalysts was filtered through celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto remove the solvent
  5. customPurification by chromatographing over 35 g
  6. customgave 384 g

Sources & evidence

ORD record
ord-174ecc59ccd14448bd13823af018c7af
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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