18-Crown-6 → [1-(2-Bromoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

HRID 851780ノート

反応式

HRID 851780 の反応式
CS(O[CH2:6][CH2:7][N:8]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.[Br-:24].[Li+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[Br:24][CH2:6][CH2:7][N:8]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 2855718-Crown-6HCID 82050Lithium BromideHCID 86736835[1-[2-[(Methylsulfonyl)oxy]ethyl]-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

生成物 1

HCID 86736837[1-(2-Bromoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

3.4 g. of the ethyl ester product from part (b) are dissolved in 100 ml. of acetone. 1.3 g. (50% excess) of lithium bromide and 0.1 g. of 18-Crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane) are added and the mixture is stirred for three hours at 50°. After the reaction has been completed as determined by TLC, the solvent is distilled off and the reaction mixture is taken up in 50 ml. of methylene chloride and shaken with 50 ml. of water. The organic phase is dried and concentrated to yield the crude product as an oil which, after scratching, crystallizes in several hours. Recrystallization from isopropanol yields purified [1-(2-bromoethyl)-2-(phenylmethylene)hydrazino]-oxoacetic acid, ethyl ester; m.p. 56°-57°.

後処理

  1. distillationthe solvent is distilled off
  2. stirringof methylene chloride and shaken with 50 ml
  3. customThe organic phase is dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-c096b4d3def441c0a9ffc1de43054507
出典データセット
uspto-grants-1983_05
特許番号
US04386199

反応ノート

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