1,1'-Thiocarbonyldiimidazole → Imidazole

HRID 491617Notes

Reaction equation

HRID 491617 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]([NH2:19])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:20]1[N:24]=[CH:23][N:22]([C:25](N2C=NC=C2)=[S:26])[CH:21]=1>C(Cl)Cl>[N:19]([C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=1)[O:8][CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[C:25]=[S:26].[NH:22]1[CH:21]=[CH:20][N:24]=[CH:23]1

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 69017105HCID 69017105, compound

Product 2

HCID 795ImidazoleHCID 17755510HCID 17755510, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with 3-(2-pyrrolin-1-yl-ethoxy)-5-trifluoromethyl-phenylamine (Step C), (560.0 mg, 2 mmol) and CH2Cl2 (10 mL) and placed in an ice bath. To this solution, 1,1-thiocarbonyldiimidazole (463 mg, 2.6 mmol) was added and the reaction was warmed to RT. After 4 h, the solvent was concentrated in vacuo and the residual yellow solid was titrated with acetone to yield the title compound as a 1/1 mixture with imidazole. This mixture was used directly in the next step.

Workup

  1. customplaced in an ice bath
  2. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-e2ae1e5812504ae5b3c9a1aacb29df28
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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