N-Hydroxy-3,4,5-trimethoxybenzamide → 4,4-Diethyl-2-(3,4,5-trimethoxybenzoyl)-3,5-isoxazolidinedione

HRID 358975

反応式

HRID 358975 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[C:6]([NH:8][OH:9])=[O:7].[CH2:17]([C:19]([CH2:26][CH3:27])([C:23](Cl)=[O:24])[C:20](Cl)=[O:21])[CH3:18]>>[CH3:16][O:15][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:12]=1[O:13][CH3:14])[C:6]([N:8]1[C:20](=[O:21])[C:19]([CH2:26][CH3:27])([CH2:17][CH3:18])[C:23](=[O:24])[O:9]1)=[O:7]

参加物

3

反応物 2

HCID 237472N-Hydroxy-3,4,5-trimethoxybenzamideHCID 4149059Diethylmalonyl dichloride

生成物 1

HCID 1302484,4-Diethyl-2-(3,4,5-trimethoxybenzoyl)-3,5-isoxazolidinedione収率 81.5%

実験手順

A mixture consisting of 2.27 g (0.0100 mol) of 3,4,5-trimethoxybenzohydroxamic acid (recrystallized from absolute ethanol prior to the reaction), 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 2.00 g (0.0101 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 of the hydroxamic acid had dissolved. The solution was extracted three times with 50 ml portions of water, four times 50 ml portions of 5% hydrochloric acid, and two times with 50 ml portions of 5% sodium carbonate. The methylene chloride solution was dried (MgSO4) and evaporated to dryness under reduced pressure to give 2.86g (81.5%) of crude 2-(3,4,5-trimethoxybenzoyl)-4,4-diethylisoxazolidine-3,5-dione; as a solid residue: mp 103-106° C. Recrystallization of 2.72 g of the crude product from 20 ml of absolute ethanol gave 2.14 g of 2-(3,4,5-trimethoxybenzoyl)-4,4-diethylisoxazolidine-3,5mp 107- 109.5° C.

後処理

  1. customrecrystallized from absolute ethanol
  2. customto the reaction), 5 ml of pyridine, and 100 ml of methylene chloride
  3. customwas prepared in a 250 ml round-bottom flask
  4. temperatureThe mixture was cooled in an ice bath
  5. dissolutionhad dissolved
  6. extractionThe solution was extracted three times with 50 ml portions of water, four times 50 ml portions of 5% hydrochloric acid, and two times with 50 ml portions of 5% sodium carbonate
  7. dry with materialThe methylene chloride solution was dried (MgSO4)
  8. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-3eb402dceb7b48f3af4988e1b58b3a38
出典データセット
uspto-grants-1991_03
特許番号
US04999366

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