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Methyl nitrite → 4-{4-[4-(3-Cyano-3-hydroxyimino-propenyl)-benzyl]-phenyl}-2-hydroxyimino-but-3-enenitrile

HRID 48137
ノート
印刷プレビュー

反応式

HRID 48137 の反応式
[OH-].[Na+].[C:3]([CH2:5][CH:6]=[CH:7][C:8]1[CH:25]=[CH:24][C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][CH2:21][C:22]#[N:23])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)#[N:4].[N:26]([O:28]C)=O.[N:30]([O-])=[O:31].[Na+]>CO>[C:22]([C:21](=[N:26][OH:28])[CH:20]=[CH:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11]2[CH:24]=[CH:25][C:8]([CH:7]=[CH:6][C:5](=[N:30][OH:31])[C:3]#[N:4])=[CH:9][CH:10]=2)=[CH:18][CH:17]=1)#[N:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 12231Methyl nitriteHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 570915964-{4-[4-(3-Cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile

生成物 1

HCID 867593594-{4-[4-(3-Cyano-3-hydroxyimino-propenyl)-benzyl]-phenyl}-2-hydroxyimino-but-3-enenitrile収率 76%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒
2 回

実験手順

A solution of sodium hydroxide (0.8 g; 0.02 mol) in 30 ml of methanol is added to a suspension of 4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile (3.0 g; 0.01 mol), prepared as described in example 6.2, in 20 ml of methanol. Methyl nitrite, generated from 2.07 g (0.03 mol) of sodium nitrite as described in example 2.2, is bubbled through the suspension at 2° C. for 25 min, and the mixture is then left at room temperature for 48 h. The solvent is then evaporated, the residue is dissolved in 200 ml of water, extracted with toluene (the extract is discarded), and acidified with conc. hydrochloric acid. The beige precipitate is taken up in ethyl acetate, washed neutral with water, dried (MgSO4) and concentrated by evaporation. 2.7 g (76%) of 4-{4-[4-(3-cyano-3-hydroxyimino-propenyl)-benzyl]-phenyl}-2-hydroxyimino-but-3-enenitrile are obtained as a light brown solid, melting point 142-145° C. (dec).

後処理

  1. customprepared
  2. customis bubbled through the suspension at 2° C. for 25 min
  3. customThe solvent is then evaporated
  4. dissolutionthe residue is dissolved in 200 ml of water
  5. extractionextracted with toluene (the extract
  6. washwashed neutral with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-696874186176498ab615d634fcfa74ee
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06703182B1

反応ノート

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