Pyridine → HCID 57265169、化合物

HRID 1492448ノート

反応式

HRID 1492448 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 57265169HCID 57265169、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

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-7f20366d04be4e65a4790de1941e21f7
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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