Pyridine → HCID 57229176, 화합물

HRID 1492451노트

반응식

HRID 1492451 반응식
[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

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 821294-Nitrophenyl chloroformateHCID 18950796HCID 18950796, 화합물

생성물 1

HCID 57229176HCID 57229176, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e56338b90d9a423eb7078358849c0aea
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05374643

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