1,3-Cyclohexanedione → Cyclohexenone-3-yl 3,4-dimethylbenzothiazol-2-one-5-carboxylate

HRID 1071909ノート

反応式

HRID 1071909 の反応式
[CH3:1][N:2]1[C:6]2[C:7]([CH3:14])=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][C:3]1=[O:15].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH2:17]1.C(N=C=NCCCN(C)C)C>C(#N)C>[CH3:1][N:2]1[C:6]2[C:7]([CH3:14])=[C:8]([C:11]([O:13][C:16]3[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=3)=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][C:3]1=[O:15]

参加物

5

反応物 3

HCID 104341,3-CyclohexanedioneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 223900833,4-Dimethylbenzothiazol-2-one-5-carboxylic acid

生成物 1

HCID 22390079Cyclohexenone-3-yl 3,4-dimethylbenzothiazol-2-one-5-carboxylate収率 48%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

1.1 g (5 mmol) of 3,4-dimethylbenzothiazol-2-one-5-carboxylic acid, 0.58 g of 1,3-cyclohexanedione and 1.25 g of ethyl(3′-dimethylaminopropyl)carbodiimide were dissolved in 40 ml of acetonitrile, and the solution was stirred at 50° C. for 4 hours. After the reaction had ended, the precipitate was filtered off and the solution was concentrated. The residue was taken up in water and extracted with methylene chloride. The organic phase was washed and dried and the solvent was then removed. Chromatography of the residue on silica gel (mobile phase: cyclohexane/ethyl acetate, gradient from 100:0 to 50:50) gave 0.77 g (2.4 mmol, 48% yield) of cyclohexenone-3-yl 3,4-dimethylbenzothiazol-2-one-5-carboxylate of m.p. 144° C.-146° C.

後処理

  1. filtrationthe precipitate was filtered off
  2. concentrationthe solution was concentrated
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed
  5. customdried
  6. customthe solvent was then removed

出典と根拠

ORDレコード
ord-cba5ab31c6c74983812493c3eb7ae34b
出典データセット
uspto-grants-2005_06
特許番号
US06908884B2

反応ノート

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