Dimethylformamide → HCID 178507320, compound

HRID 1155539Notes

Reaction equation

HRID 1155539 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10](S)[NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.CN(C)C=O>[Ni].C(Cl)(Cl)Cl.CO>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 178507321HCID 178507321, compound

Product 1

HCID 178507320HCID 178507320, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584188Chloroform methanolSolvent

Procedure

To a solution of 2.3 g. (12 mmoles) of 4-(2-amino-4-pyridyl)imidazole-2-thiol in 60 ml. of dimethylformamide was added 8 g. of Raney nickel and the mixture heated at 115° C. for 3 hours. The mixture was filtered and the filtrate concentrated to a brown solid. After trituration with boiling chloroform, the solid was taken up in 50 ml. of absolute ethanol, treated with charcoal and the filtered solution concentrated to a small volume. The precipitate was filtered and dried, 1.12 g. (60%), m.p. 193°-196° C. The analytical sample was prepared by chromatographing on Florisil TM using chloroform-methanol (9:1, v:v) as the eluent, m.p. 196°-198° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated to a brown solid
  3. additionof absolute ethanol, treated with charcoal
  4. concentrationthe filtered solution concentrated to a small volume
  5. filtrationThe precipitate was filtered
  6. customdried
  7. customThe analytical sample was prepared by chromatographing on Florisil TM

Sources & evidence

ORD record
ord-4a6d4255ea6541bc93eb3ba7d00f4d5a
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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