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

HRID 1709038

反応式

HRID 1709038 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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=O), 1747 (s, C=O), 1695 cm-1 (s, C=O);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.

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. 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

出典と根拠

ORDレコード
ord-d74d39c2921b4789a28119d5b7ea547c
出典データセット
uspto-grants-1990_08
特許番号
US04946963

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