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

HRID 1071909노트

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HRID 1071909 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cba5ab31c6c74983812493c3eb7ae34b
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908884B2

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