3-Hydroxypicolinamide → 3-Hydroxythiopicolinamide

HRID 1638313Notes

Reaction equation

HRID 1638313 reaction equation
[OH:1][C:2]1[C:3]([C:8]([NH2:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1>O1CCOCC1>[OH:1][C:2]1[C:3]([C:8]([NH2:10])=[S:20])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702773-HydroxypicolinamideHCID 87949Lawesson's reagent

Product 1

HCID 1360468883-HydroxythiopicolinamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 3-hydroxypicolinamide (1 g) and Lawesson's reagent (2 g) in dry dioxane (75 ml) was allowed to react under Argon atmosphere at 95° C. for 4 hours. Then, insoluble solids in the reaction mixture was filtered off with suction and the filtrate was concentrated. The residue was dissolved in methylene chloride and purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1). The second yellow fraction was concentrated. the residual solids were recrystallized from CHCl3 -n-hexane to give yellow crystals of 3-hydroxythiopicolinamide (546 mg, 46%), m.p. 150°-151° C.

Workup

  1. customto react under Argon atmosphere at 95° C. for 4 hours
  2. filtrationThen, insoluble solids in the reaction mixture was filtered off with suction
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in methylene chloride
  5. custompurified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
  6. concentrationThe second yellow fraction was concentrated
  7. customthe residual solids were recrystallized from CHCl3 -n-hexane

Sources & evidence

ORD record
ord-1830a1ae8baa4bcdb05ed5fb8361280c
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

Loading…