Pyridine → 2-Benzoyl-4,4-diethylisoxazolidine-3,5-dione

HRID 358976

反応式

HRID 358976 の反応式
[C:1]([NH:9][OH:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:17]([C:19]([CH2:26][CH3:27])([C:23](Cl)=[O:24])[C:20](Cl)=[O:21])[CH3:18]>C(Cl)Cl>[C:1]([N:9]1[C:20](=[O:21])[C:19]([CH2:26][CH3:27])([CH2:17][CH3:18])[C:23](=[O:24])[O:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 10313Benzohydroxamic acid2 回HCID 4149059Diethylmalonyl dichloride

生成物 1

HCID 148511932-Benzoyl-4,4-diethylisoxazolidine-3,5-dione収率 75.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture consisting of 1.37 g (0.0100 mol) of benzohydroxamic acid, 10 ml of pyridine, and 100 ml of methylene chloride was prepared in a 250 ml round-bottom flask. The mixture was cooled in an ice bath and 2.00 g (0.101 mol) of diethylmalonyl chloride was added dropwise over a 15 minute period. The reaction mixture was stirred for one hour at room temperature after which time all the benzohydroxamic acid had dissolved. The solution was evaporated under reduced pressure, and to the residue was added 100 ml of cold water. The insoluble viscous oil was rubbed with a glass rod to effect solidification. The solid was filtered and dried to give 1.89 g (75.9%) of crude 2-benzoyl-4,4-diethylisoxazolidine-3,5-dione: mp 76-79° C. Recrystallization of 1.72 g of crude isoxazolidine-3,5-dione from 20 ml of absolute ethanol gave 1.56 g of pure 2-benzoyl-4,4-diethylisoxazolidine-3,5-dione: mp 87-88° C. (lit 87-88° C.) G. Zinner and R. Moll, Arch. Pharm., 299. (6), 562-8(1966), CA 65 10575f; IR (Nujol) 1817 (s, C=0), 1762 (s, C=0), 1714 (s, C=0) and 694 (s, aromatic C-H bend) cm-1 ; NMR (acetone-d6) δ 7.46 (m, 5, aromatic C--H), 1.87 (q, 4, CH2), 1.00 (t, 6, CH3).

後処理

  1. customwas prepared in a 250 ml round-bottom flask
  2. temperatureThe mixture was cooled in an ice bath
  3. dissolutionhad dissolved
  4. customThe solution was evaporated under reduced pressure
  5. additionto the residue was added 100 ml of cold water
  6. filtrationThe solid was filtered
  7. customdried

出典と根拠

ORDレコード
ord-0813a96ecff34b26b72ca960f3f6a9b3
出典データセット
uspto-grants-1991_03
特許番号
US04999366

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