1,1'-Thiocarbonyldiimidazole → HCID 11358291, compound

HRID 1066158Notes

Reaction equation

HRID 1066158 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[C:15](N1C=CN=C1)([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=S>O1CCOCC1>[N:17]1([C:15]2[NH:1][C:2]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=3[S:11](=[O:14])(=[O:13])[N:12]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 114016534-Amino-3-sulfamoylbenzoic acid

Product 1

HCID 11358291HCID 11358291, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Amino-3-sulfamoylbenzoic acid (6 g) and thiocarbonyldiimidazole (23.2 g) in dioxane (60 mL) was refluxed for 2 h. The solvent was removed by distillation under reduced pressure. The residue was dispersed in water (200 mL) and supplemented with a 10% aqueous solution of NaOH (40 mL). After stirring for 30 min. at room temperature, the solution was treated with charcoal, filtered, and the filtrate was adjusted to pH 2 with 12N HCl. The resulting precipitate was collected by filtration, washed with water and dried to give the title compound (yield: 4.5 g); m.p. >300° C.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionThe residue was dispersed in water (200 mL)
  3. additionthe solution was treated with charcoal
  4. filtrationfiltered
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-975372a9bd984164870462b3022ed83e
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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