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

HRID 358978

반응식

HRID 358978 반응식
[CH3:1][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>[CH3:1][C:2]1[CH:3]=[CH:4][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:10][CH:11]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 426839N-hydroxy-4-methylbenzamideHCID 4149059Diethylmalonyl dichloride

생성물 1

HCID 104686282-(4-Methylbenzoyl)4,4-diethylisoxazolidine-3,5-dione수율 34.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture consisting of 1.51 g (0.0100 mol) of 4-methylbenzohydroxamic acid, mp 148-150° C. (dec.) (lit. mp 148° C. dec. , Beilstein Handbook of Organic Chemistry, series H, vol 9, p. 491), 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 1.977 g (0.0100 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 0.94 g (34.2%) of crude 2-(4-methylbenzoyl)-4,4-diethylisoxazolidine-3,5-dione as a solid residue. Recrystallization of the solid from methanol gave pure 2-(4-methylbenzoly)-4,4-diethylisoxazolidine-3,5-dione as a white solid: mp 92-93° C.; IR (Nujol) 1805 (s,C=0), 1747 (s, C=0) 1695 cm-1 (s, C=0);H1NMR (400 MHz, CDCl3) δ7.70 (d,2H), 7.29 (d,2H), 2.43 (s,3H), 1.95 (q. 4H), 1.00 (t, 6H); High resolution MS, calc'd for: C15H17NO4 : 275.1157. Found: 275.1163. Anal. Calc'd for: C15H17NO4 : C, 65.44; H, 6.23; N 5 09. Found: C, 65.24; H, 6.45; N, 5.28.

후처리

  1. customwas prepared in a 250 ml round bottom flask
  2. temperatureThe mixture was cooled in an ice bath
  3. dissolutionhad dissolved
  4. 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
  5. dry with materialThe methylene chloride was dried (MgSO4)
  6. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-49692508af8b48958e1298a4cc854621
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04999366

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