Pyridine → HCID 57229176、化合物

HRID 1492451ノート

反応式

HRID 1492451 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=NOC=2)=[CH:4][CH:3]=1.CN(C=[O:17])C.[N:18]1[CH:23]=CC=CC=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>C(#N)C>[O:17]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25](=[O:26])[O:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[CH:7][CH:6]=2)=[N:9][CH:23]=[N:18]1

参加物

6

反応物 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 821294-Nitrophenyl chloroformateHCID 18950796HCID 18950796、化合物

生成物 1

HCID 57229176HCID 57229176、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 4-aminophenyl oxadiazole (0.97 g, 0.006 mol, compound of part A) in acetonitrile (25 mL)/DMF (2 mL) and pyridine (0.50 mL, 0.48 g, 0.006 mol) under argon at 0° C. was treated with p-nitrophenyl chloroformate (1.21 g, 0.006 mol) and was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and an effort was made to partition the remaining oil between ethyl acetate and 10% citric acid, resulting in separation of a solid insoluble in either phase. The solid was collected and triturated with anhydrous ether and dried in vacuo to yield 1.67 g of the title compound, m.p. 210°-212° C. TLC, silica gel, EtOAc/hexanes (2:1), Rf =0.58; M.S. (M+H)+ at 327, M.W. 326. This compound contained minor impurities and was used without further purification.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto partition the remaining oil between ethyl acetate and 10% citric acid
  3. customresulting in separation of a solid insoluble in either phase
  4. customThe solid was collected
  5. customtriturated with anhydrous ether
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-e56338b90d9a423eb7078358849c0aea
出典データセット
uspto-grants-1994_12
特許番号
US05374643

反応ノート

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