Bromine → HCID 90092744、化合物

HRID 1774573ノート

反応式

HRID 1774573 の反応式
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]

参加物

9

反応物 4

HCID 24408BromineHCID 517045Sodium AcetateHCID 5360545SodiumHCID 90092588HCID 90092588、化合物

生成物 1

HCID 90092744HCID 90092744、化合物収率 98.3%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒2 回HCID 1140Toluene溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c19b0524670842dd8906f63e2f021501
出典データセット
uspto-grants-2016_02
特許番号
US09260395B2

反応ノート

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