1,1'-Thiocarbonyldiimidazole → HCID 11128090, compound

HRID 481961Notes

Reaction equation

HRID 481961 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[NH2:12])(=[O:5])=[O:4].[C:13](N1C=CN=C1)(N1C=CN=C1)=[S:14]>O1CCOCC1.CN(C=O)C>[CH3:1][N:2]1[C:13](=[S:14])[NH:12][C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[S:3]1(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 10910271HCID 10910271, compound

Product 1

HCID 11128090HCID 11128090, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-methyl-4-aminopyridine-3-sulfonamide (de Tullio et al., Tetrahedron 1995, 3221-3234) (5.0 g) and thiocarbonyidiimidazole (7.5 g) in dioxane (30 mL) and DMF (15 mL) was heated at 90° C. for 2 h. The solvents were removed by distillation under reduced pressure. The residue was dispersed in 0.6N NaOH (20 mL) and stirred for 30 min. The alkaline solution was treated with charcoal, filtered, and the filtrate was adjusted to pH 4-5. The precipitate was collected by filtration, washed with water and dried (yield: 4 g); m.p. 195°-198° C. (Compound IV).

Workup

  1. customThe solvents were removed by distillation under reduced pressure
  2. additionThe residue was dispersed in 0.6N NaOH (20 mL)
  3. additionThe alkaline solution was treated with charcoal
  4. filtrationfiltered
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried (yield: 4 g)

Sources & evidence

ORD record
ord-bf7e030a5baa43118a19f98f38349a8a
Source dataset
uspto-grants-1998_08
Patent number
US05792764

Reaction notes

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