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

HRID 1993746ノート

反応式

HRID 1993746 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.)

後処理

  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

出典と根拠

ORDレコード
ord-3d74aca253784cce9e1719101bc94c28
出典データセット
uspto-grants-2010_01
特許番号
US07652018B2

反応ノート

読み込み中…