Pyridine → HCID 57265169, 화합물

HRID 1492448노트

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HRID 1492448 반응식
[O:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=2)=[N:4][CH:3]=[N:2]1.N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21]>C(#N)C>[O:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:20](=[O:21])[O:22][C:23]3[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=3)[CH:9]=[CH:10][CH:11]=2)=[N:4][CH:3]=[N:2]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 189507763-(1,2,4-Oxadiazol-5-yl)aniline

생성물 1

HCID 57265169HCID 57265169, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 3-(1,2,4-oxadiazol-5-yl)phenyl amine (0.97 g, 0.006 mol, prepared in sequence by the procedures described in Lin et al. J. Org. Chem., 1979, 44, 4160 and Lin et al., J. Org. Chem., 1979, 44, 4160) in acetonitrile (25 mL) and pyridine (0.97 mL, 0.95 g, 0.012 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 1.54 g of [3-(1,2,4-oxadiazol-5-yl)]phenylcarbamic acid, 4-nitrophenyl ester, m.p. 195°-197° C. TLC, silica gel, EtOAc/MeOH (20:1), Rf =0.75; 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-7f20366d04be4e65a4790de1941e21f7
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05374643

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