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

HRID 1993746노트

반응식

HRID 1993746 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.)

후처리

  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

출처 및 근거

ORD 기록
ord-3d74aca253784cce9e1719101bc94c28
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652018B2

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