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

HRID 1709037Notes

Reaction equation

HRID 1709037 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][OH:10])=[O:8])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:19]([C:21]([CH2:28][CH3:29])([C:25](Cl)=[O:26])[C:22](Cl)=[O:23])[CH3:20]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:22](=[O:23])[C:21]([CH2:28][CH3:29])([CH2:19][CH3:20])[C:25](=[O:26])[O:10]2)=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 221131N-Hydroxy-4-methoxybenzamideHCID 4149059Diethylmalonyl dichloride

Product 1

HCID 100171482-(4-Methoxybenzoyl)-4,4-diethylisoxazolidine-3,5-dioneYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 1.67 g (0.0107 mol) of 4-methoxybenzohydroxamic acid, mp 158°-15920 C. (dec.)(lit. mp 156°-157° C. (dec.), Beilstein Handbook of Organic Chemistry, series H, vol 10, p. 170), 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 2.107 g (0.0107 mol) of diethylmalonyl chloride was added dropwise over a 15 minute period with stirring. The reaction mixture was stirred for 2 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 of 5% sodium carbonate. The methylene chloride was dried (MgSO4) and evaporated to dryness under reduced pressure to give 2.19 g (70.4%) of crude 2-(4-methoxybenzoyl)-4,4-diethylisoxazolidine-3,5-dione as a solid residue. Recrystallization of the solid from absolute ethanol gave pure 2-(4-methoxybenzoyl)-4,4-diethylisoxazolidine-3,5-dione as a white solid: mp 116°-118° C.; IR (Nujol) 1810 (s,C=O), 1750 (s, C=O), 1690 cm-1 (s, C=O); 1H NMR (400 MHz, CDCl3) 7.83 (d, 2H), 6.98 (d, 2H), 3.89 (t, 3H), 1.95 (q, 4H), 1.01 (t, 6H); High resolution MS, calc'd for: C15H17NO5 : 291.1102. Found: 291.1106. Anal. Calc' d for: C15H17NO5 : C, 61.84; H, 5.88; N, 4.81. Found: C, 61.83; H, 5.76; N, 4.76.

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 of 5% sodium carbonate
  4. dry with materialThe methylene chloride was dried (MgSO4)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a80abc98edcf4730af0c2b79e350e6b8
Source dataset
uspto-grants-1990_08
Patent number
US04946963

Reaction notes

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