1,1'-Thiocarbonyldiimidazole → HCID 53642643, compound

HRID 1383676Notes

Reaction equation

HRID 1383676 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-555acb7d028c48f983644b3097903f7b
Source dataset
uspto-grants-2001_07
Patent number
US06255349B1

Reaction notes

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