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1-Bromopropane → (Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

HRID 517598
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HRID 517598 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[NH:17][C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][CH3:27]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[N:17]([CH2:25][CH2:26][CH3:27])[C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

생성물 1

HCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Potassium carbonate (93 mg, 0.60 mmol) was added to a solution of compound 2 (75 mg, 0.30 mmol) in 3 mL of anhydrous DMF at 0° C. After stifling of the reaction mixture for 20 min, a solution of 1-bromopropane (30 μL, 0.33 mmol) in 1 mL of anhydrous DMF was added and then the reaction mixture was stirred at room temperature overnight. The reaction was quenched by adding water and extracted with ethyl acetate. The ethyl acetate layer was washed with water (4×20 mL) and dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (15% ethyl acetate in hexanes) to afford 82 mg (93.9%) as a light-yellow solid.

후처리

  1. customThe reaction was quenched
  2. additionby adding water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water (4×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica column chromatography (15% ethyl acetate in hexanes)
  9. customto afford 82 mg (93.9%) as a light-yellow solid

출처 및 근거

ORD 기록
ord-939dcc066a6046ebb1f4f823fb93bf45
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115122B2

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