1,1'-Thiocarbonyldiimidazole → HCID 178515269, compound

HRID 129479Notes

Reaction equation

HRID 129479 reaction equation
[NH2:1][C:2]1[C:3](=[O:19])[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[C:10]([C:11]=1[NH2:12])=[CH:9][CH:8]=[CH:7][N:6]=2.[C:20](N1C=CN=C1)(N1C=CN=C1)=[S:21]>O1CCCC1>[SH:21][C:20]1[NH:1][C:2]2[C:3](=[O:19])[N:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]3[N:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 10467376HCID 10467376, compound

Product 1

HCID 178515269HCID 178515269, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 102 (2.0 g, 7.9 mmol) was then suspended in 80 ml of tetrahydrofuran, and 2.3 g (13 mmol) of thiocarbonyldiimidazole was added to the suspension. The mixture was heated to reflux for 2 hours. The solvent was distilled off under reduced pressure, and the residue was triturated with ethanol. The formed crystals were taken by filtration. Recrystallization from DMF gave 1.1 g (yield 47%) of Compound 20 as colorless crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was triturated with ethanol
  5. filtrationThe formed crystals were taken by filtration
  6. customRecrystallization from DMF

Sources & evidence

ORD record
ord-7666a874cee14a6fa9b4a9d96ddf9c5b
Source dataset
uspto-grants-1995_11
Patent number
US05468756

Reaction notes

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