Acetaldehyde → Methyl 3-carboxy-3-(2-ethylidene-1-methylhydrazino)-propionate triethylamine salt

HRID 1379221

反応式

HRID 1379221 の反応式
[CH3:1][NH:2][NH2:3].[CH3:4][O:5][C:6](=[O:12])/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10].[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[CH:20](=O)[CH3:21]>C1COCC1>[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[C:9]([CH:8]([N:2]([CH3:1])[N:3]=[CH:20][CH3:21])[CH2:7][C:6]([O:5][CH3:4])=[O:12])([OH:11])=[O:10]

参加物

6

反応物 4

HCID 177AcetaldehydeHCID 6061MethylhydrazineHCID 8471TriethylamineHCID 5354456Monomethyl maleate

生成物 1

HCID 86751281Methyl 3-carboxy-3-(2-ethylidene-1-methylhydrazino)-propionate triethylamine salt

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 88.5 g methylhydrazine (1.92 moles) in 340 ml THF is added at +25° C. to a solution of 250 g maleic acid monomethyl ester (1.92 moles) and 194.5 g triethylamine (1.92 moles) in 1850 ml THF. During the addition a precipitation of the triethylamine salt of the intermediate methyl 3-carboxy-3-(1-methyl-hydrazino)-propionate is formed. After stirring for 2 hours at +25° C., a solution of 101.6 g acetaldehyde (2.3 moles) in 370 ml THF is added at +25° C. The precipitation dissolves during the addition. After stirring for 1 hour at +25° C. the solution is evaporated completely. To remove traces of water or methanol, the residue is mixed with 750 ml toluene and evaporated again completely (10 mbar, 60° C.). Yield: 429.6 g of methyl 3-carboxy-3-(2-ethylidene-1-methylhydrazine)-propionate triethylamine salt as viscous yellow oil (83%).

後処理

  1. additionDuring the addition
  2. customa precipitation of the triethylamine salt of the intermediate methyl 3-carboxy-3-(1-methyl-hydrazino)-propionate
  3. customis formed
  4. customThe precipitation
  5. dissolutiondissolves during the addition
  6. stirringAfter stirring for 1 hour at +25° C. the solution
  7. customis evaporated completely
  8. customTo remove traces of water or methanol
  9. additionthe residue is mixed with 750 ml toluene
  10. customevaporated again completely (10 mbar, 60° C.)

出典と根拠

ORDレコード
ord-279630d299214a238c1364dceb47b59d
出典データセット
uspto-grants-1997_09
特許番号
US05670648

関連ノート

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