Pyridine → 2-(4-Chlorobenzoyl)-4,4-diethylisoxazolidine-3,5-dione

HRID 358979

Reaction equation

HRID 358979 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][OH:9])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:18]([C:20]([CH2:27][CH3:28])([C:24](Cl)=[O:25])[C:21](Cl)=[O:22])[CH3:19]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([N:8]2[C:21](=[O:22])[C:20]([CH2:27][CH3:28])([CH2:18][CH3:19])[C:24](=[O:25])[O:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5871784-Chlorobenzenehydroxamic acidHCID 4149059Diethylmalonyl dichloride

Product 1

HCID 148511942-(4-Chlorobenzoyl)-4,4-diethylisoxazolidine-3,5-dioneYield 16.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 2.70 g (0.0157 mol) of 4-chlorobenzohydroxamic acid, mp 170-171° C. (dec). (lit. mp 168° C. dec., Bielstein Handbook of Organic Chemistry, series H, vol 9. p. 341), 5 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 3.097 g (0.0157 mol) of diethylmalonyl chloride was added dropwise over a 15 minutes period with stirring. The reaction mixture was stirred for 4 hours at room temperature after which time all the hydroxamic acid had dissolved. The solution was extracted two times with 50 ml portions of water, three times with 50 ml portions of 5% hydrochloric acid, and two times with 50 ml portions for 5% sodium carbonate. The methylene chloride was dried (MgSO4) and evaporated to dryness under reduced pressure to give 0.76 g (16.4%) of crude 2-(4-chlorobenzoyl)-4,4-diethylisoxazolidine-3,5-dione as a solid residue. Recrystallization of the solid from methanol gave pure 2-(4-chlorobenzoyl)-4,4-diethylisoxazolidine-3,5-dione as a white solid: mp 98-100° C.; IR (Nujol) 1812 (s, C=0) 1745 (s C=0) 1700 cm-1 (s, C=0); 1H NMR (400 MHz, CDCl3) 7.77-7.80 (m, 2H), 7.49-7.52 (m, 2H), 1.99 (q/ 4H), 1.04 (t, 6H); High resolution MS, calc'd for: C14H14NO4 -Cl: 295.0612. Found: 295.0615. Anal. Calc'd for: C14H14NO4Cl: C, 56.86; H, 4.77; N, 4.74; Cl, 11.99. Found: C, 57.04; H, 4.63; N, 4.58; Cl, 11.88.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. dissolutionhad dissolved
  3. extractionThe solution was extracted two times with 50 ml portions of water, three times with 50 ml portions of 5% hydrochloric acid, and two times with 50 ml portions for 5% sodium carbonate
  4. dry with materialThe methylene chloride was dried (MgSO4)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1132bb5ca8ee4153a6a1eeeed30a122a
Source dataset
uspto-grants-1991_03
Patent number
US04999366

Linked notes

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