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Methylparaben → 4-(6-Chloro-pyridazin-3-yloxy)-benzoic acid methyl ester

HRID 215836
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HRID 215836 반응식
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1>C1COCC1.O>[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:22]2[N:21]=[N:20][C:19]([Cl:18])=[CH:24][CH:23]=2)=[CH:12][CH:11]=1
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참가 물질

6

반응물 3

HCID 7456MethylparabenHCID 673313,6-DichloropyridazineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 606748904-(6-Chloro-pyridazin-3-yloxy)-benzoic acid methyl ester수율 66%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Potassium tert-butoxide (0.87 g, 7.75 mmol) was added in portions to a solution of 4-hydroxybenzoic acid methyl ester 1 (1.15 g, 7.56 mmol) in anhydrous THF (25 ml). The mixture was stirred at room temperature for 30 minutes, then 3,6-dichloro-pyridazine (1.12 g, 7.56 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and heated at reflux for 14 h. The mixture was cooled to room temperature and diluted with water (100 ml). The formed precipitate was collected by filtration, washed with water and dried to obtain 1.315 g (66%) of 4-(6-chloro-pyridazin-3-yloxy)-benzoic acid methyl ester which was used for the next step without further purification.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. temperatureheated
  3. temperatureat reflux for 14 h
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationThe formed precipitate was collected by filtration
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-f51d8c5533534c11a21084511f6f8491
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193192B2

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