Bromine → HCID 90092744, 화합물

HRID 1774573노트

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HRID 1774573 반응식
C([O-])(=O)C.[Na+].[CH3:6][O:7][CH:8]([O:19][CH3:20])[C:9]1[NH:13][N:12]=[C:11]([C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:10]=1.[Br:21]Br.[Na]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl.C1(C)C=CC=CC=1>[Br:21][C:10]1[C:11]([C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[N:12][NH:13][C:9]=1[CH:8]([O:7][CH3:6])[O:19][CH3:20]

참가 물질

9

반응물 4

HCID 24408BromineHCID 517045Sodium AcetateHCID 5360545SodiumHCID 90092588HCID 90092588, 화합물

생성물 1

HCID 90092744HCID 90092744, 화합물수율 98.3%

시약·촉매·용매 4

HCID 176Acetic Acid용매2회HCID 1140Toluene용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

Sodium acetate (0.26 g, 3.17 mmol) was added to a solution of 2-[5-(dimethoxymethyl)-1H-pyrazol-3-yl]-1,3-thiazole (8b) (714 mg, 3.17 mmol) in chloroform (7.7 mL) and acetic acid (7.7 mL). The mixture was stirred at room temperature for 1 hour. After cooling to 0° C., a solution of bromine (0.155 mL, 3.01 mmol) in acetic acid (1.8 mL) was added dropwise. The reaction mixture was stirred at the same temperature for 40 minutes before being diluted with dichloromethane (10 mL). The mixture was neutralized with 2N sodium hydroxyde to pH 6. The layers were separated and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic layers were dried over sodium sulfate, concentrated in vacuo, and co-evaporated with toluene to provide 2-[4-bromo-5-(dimethoxymethyl)-1H-pyrazol-3-yl]-1,3-thiazole (8c) (900 mg, 2.96 mmol, 93%) which was used without further purification.

후처리

  1. temperatureAfter cooling to 0° C.
  2. stirringThe reaction mixture was stirred at the same temperature for 40 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (10 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c19b0524670842dd8906f63e2f021501
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260395B2

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