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

HRID 358976

Reaction equation

HRID 358976 reaction equation
[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

Participants

5

Reactant 3

HCID 1049PyridineHCID 10313Benzohydroxamic acid2×HCID 4149059Diethylmalonyl dichloride

Product 1

HCID 148511932-Benzoyl-4,4-diethylisoxazolidine-3,5-dioneYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0813a96ecff34b26b72ca960f3f6a9b3
Source dataset
uspto-grants-1991_03
Patent number
US04999366

Linked notes

Loading…