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Water → 3-[3-(2-Aminopyridin-3-yloxy)propyl]thiazolidine-2,4-dione

HRID 357145
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HRID 357145 반응식
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11]Cl)=[CH:6][CH:5]=[CH:4][N:3]=1.[Na].[S:14]1[CH2:18][C:17](=[O:19])[NH:16][C:15]1=[O:20].[I-].[Na+].O>CN(C)C=O>[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][N:16]2[C:17](=[O:19])[CH2:18][S:14][C:15]2=[O:20])=[CH:6][CH:5]=[CH:4][N:3]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 5238Sodium IodideHCID 189368002-Amino-3-(3-chloropropyloxy)pyridineHCID 867387272,4-Thiazolidinedione sodium salt

생성물 1

HCID 189367993-[3-(2-Aminopyridin-3-yloxy)propyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a suspension of 9.33 g (50 mmol) of 2-amino-3-(3-chloropropyloxy)pyridine and 6.97 g (50 mmol) of thiazolidine-2,4-dione sodium salt in 200 ml of N,N-dimethylformamide, 7.49 g (50 mmol) of sodium iodide was added, followed by refluxing at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate) to yield 8.14 g (60.9%, yellow solid) of the desired product.

후처리

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. distillationafter which the solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate)

출처 및 근거

ORD 기록
ord-a122f5d4ee1141fe8b1e32748c526b27
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05840732

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