1,1'-Thiocarbonyldiimidazole → 4-[2-(4,4-Dimethyl-2-thioxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1993746Notes

Reaction equation

HRID 1993746 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[S:7])C=1.[OH:13][CH2:14][C:15]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[N:23]=1)([CH3:17])[CH3:16]>O1CCCC1>[CH3:16][C:15]1([CH3:17])[CH2:14][O:13][C:6](=[S:7])[N:18]1[C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=2)[N:23]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 866185984-{2-[(2-Hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile

Product 1

HCID 875378174-[2-(4,4-Dimethyl-2-thioxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrileYield 11.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Thiocarbonyldiimidazole (652 mg, 3.6 mmol) was added to a solution of 4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (1.0 g, 3.6 mmol), prepared in the previous step, in 60 mL of dry tetrahydrofuran at 0° C. The solution was allowed to warm to room temperature. After 2 h, starting material remained. The reaction was heated to reflux. After 12 h, the reaction was cooled to room temperature and concentrated under reduced pressure. Purification of the residue by reverse phase HPLC using a continuous gradient of 70-83% acetonitrile-water over 10 min gave the title compound (130 mg, 11%) as a tan solid. mp>240° C. (dec.)

Workup

  1. temperatureThe reaction was heated to reflux
  2. waitAfter 12 h
  3. temperaturethe reaction was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by reverse phase HPLC
  6. customover 10 min

Sources & evidence

ORD record
ord-3d74aca253784cce9e1719101bc94c28
Source dataset
uspto-grants-2010_01
Patent number
US07652018B2

Reaction notes

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