O-Xylene → HCID 86711889、化合物

HRID 1475195ノート

反応式

HRID 1475195 の反応式
[C:1]1([C:7]2[O:11][C:10]([C:12]([NH:14][NH2:15])=O)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:17](N)(=[NH:19])[CH3:18].C1(C)C(C)=CC=CC=1>>[CH3:18][C:17]1[NH:15][N:14]=[C:12]([C:10]2[O:11][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][N:9]=2)[N:19]=1

参加物

4

反応物 3

HCID 7237O-XyleneHCID 67170Acetamidine monohydrochlorideHCID 134074845-phenyl-1,3,4-oxadiazole-2-carbohydrazide

生成物 1

HCID 86711889HCID 86711889、化合物収率 22.5%

反応条件

温度
170 °C

実験手順

To a solution of 5-phenyl-1,3,4-oxadiazole-2-carbohydrazide (400 mg, 1.96 mmol) and acetamidine hydrochloride (573 mg, 6.07 mmol) in xylene (20 mL) NaOH (243 mg, 6.07 mmol) was added. The mixture was stirred at 170° C. for 36 h, and then the reaction was cooled to RT, washed with H2O (20 mL), extracted with 4:1 CHCl3:i-PrOH (5×50 mL), dried with MgSO4 and concentrated. The crude product was purified on a Biotage pre-packed silica gel column (MeOH:DCM 2% to 20% MeOH) to afford 2-(5-methyl-1H-1,2,4-triazol-3-yl)-5-phenyl-1,3,4-oxadiazole (100 mg, 22%) as a white powder. MS (ES+) C11H9N5O requires: 227 found: 228 [M+H]+.

後処理

  1. temperaturethe reaction was cooled to RT
  2. washwashed with H2O (20 mL)
  3. extractionextracted with 4:1 CHCl3
  4. dry with materiali-PrOH (5×50 mL), dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified on a Biotage pre-packed silica gel column (MeOH:DCM 2% to 20% MeOH)

出典と根拠

ORDレコード
ord-6a26af879fff433bad494a5fd297e37c
出典データセット
uspto-grants-2015_04
特許番号
US09018380B2

反応ノート

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