Acetyl chloride → 2-(4-Nitrophenyl)benzo[d]thiazol-6-yl acetate

HRID 643646ノート

反応式

HRID 643646 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[C:22](Cl)(=[O:24])[CH3:23]>C1COCC1>[C:22]([O:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[S:11][C:12]=2[CH:18]=1)(=[O:24])[CH3:23]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 108909996-Benzothiazolol, 2-(4-nitrophenyl)-

生成物 1

HCID 592629692-(4-Nitrophenyl)benzo[d]thiazol-6-yl acetate収率 98.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under N2, 24 (4.0 mmol) was dissolved in THF (100 ml) and, at 0° C., NaH (8.2 mmol) was slowly added. The mixture was stirred for 30 min at 0° C. and acetyl chloride (6.0 mmol) was added dropwise. The resulting mixture was then stirred at room temperature overnight. The reaction was hydrolyzed and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and the solvent was removed via a rotary evaporator. The residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent to yield 1.24 g (74%) of 25 as a yellow solid.

後処理

  1. stirringThe resulting mixture was then stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed via a rotary evaporator
  5. customThe residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-25e07eadc45e419c8c81cb2a002db935
出典データセット
uspto-grants-2010_04
特許番号
US07700616B2

反応ノート

読み込み中…