1,1'-Thiocarbonyldiimidazole → HCID 21197737, compound

HRID 1066151Notes

Reaction equation

HRID 1066151 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].[C:14](N1C=CN=C1)([N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=S>O1CCOCC1>[OH2:11].[Cl:8][C:6]1[C:5]([Cl:9])=[CH:4][C:3]2[S:10](=[O:12])(=[O:11])[N:13]=[C:14]([N:16]3[CH:20]=[CH:19][N:18]=[CH:17]3)[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 204803Benzenesulfonamide, 2-amino-4,5-dichloro-

Product 1

HCID 21197737HCID 21197737, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-4,5-dichlorobenzenesulfonamide (10 g) and thiocarbonyldiimidazole (22 g) in dioxane (160 mL) was refluxed for 2-3 h. The solvent was removed by distillation under reduced pressure and the residue was dispersed in water (100 mL). The addition of an aqueous solution of NaOH (16 g/160 mL) gave a solution which, after cooling, abundantly precipitated the crystalline sodium salt of the title compound. The salt was collected by filtration and dissolved in a 1:2 mixture of methanol and water (300 mL), treated with charcoal, filtered, and the filtrate was adjusted to pH 2 with 12N HCl. The precipitate was collected by filtration, washed with water and dried (yield: 11.3 g); m.p.: 312-315° C.

Workup

  1. temperaturewas refluxed for 2-3 h
  2. customThe solvent was removed by distillation under reduced pressure
  3. additionthe residue was dispersed in water (100 mL)
  4. additionThe addition of an aqueous solution of NaOH (16 g/160 mL)
  5. customgave a solution which
  6. temperatureafter cooling
  7. customabundantly precipitated the crystalline sodium salt of the title compound
  8. filtrationThe salt was collected by filtration
  9. dissolutiondissolved in a 1:2 mixture of methanol and water (300 mL)
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with water
  14. customdried (yield: 11.3 g)

Sources & evidence

ORD record
ord-09fc0556fbf64500b28852be5d600f14
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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