1,1'-Thiocarbonyldiimidazole → HCID 53642643, compound

HRID 2187171Notes

Reaction equation

HRID 2187171 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[N:24]=[N:25][S:26][CH:27]=2)=[O:22])=[CH:16][CH:15]=1>O1CCCC1>[N:13]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]2[N:24]=[N:25][S:26][CH:27]=2)=[O:22])=[CH:18][CH:19]=1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 12051700HCID 12051700, compound

Product 1

HCID 53642643HCID 53642643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a ice cooled solution of 1,1′-thiocarbonyldiimidazole (7.28 g) in tetrahydrofuran (50 mL) is added [1,2,3]-thiadiazole-4-carboxylic acid (4-amino-phenyl) amide (9.0 g) in tetrahydrofuran (100 mL). After approximately one hour the solvent is removed by evaporation and the residue is dissolved in ethyl acetate. Diethyl ether is added to precipitate the crude product, which is then collected by filtration, dissolved in dichloromethane, and passed through a plug of hydrous magnesium silicate. After removal of solvents, the residue is recrystallized from ethyl acetate-hexanes to provide the desired product as a slightly yellow solid.

Workup

  1. customAfter approximately one hour the solvent is removed by evaporation
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. additionDiethyl ether is added
  4. customto precipitate the crude product, which
  5. filtrationis then collected by filtration
  6. dissolutiondissolved in dichloromethane
  7. customAfter removal of solvents
  8. customthe residue is recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-5791a691cb0947cb93aec791f52b7815
Source dataset
uspto-grants-2002_06
Patent number
US06407249B1

Reaction notes

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