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Diisopropylamine → [2-Chloro-3-(trifluoromethyl)phenyl]methyl isocyanide

HRID 554098
ノート
印刷プレビュー

反応式

HRID 554098 の反応式
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][CH:14]=O.C(NC(C)C)(C)C.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][N+:13]#[C-:14]
参加物反応条件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 7912DiisopropylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86617531{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}formamide

生成物 1

HCID 86617532[2-Chloro-3-(trifluoromethyl)phenyl]methyl isocyanide収率 106.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
3.5 °C

実験手順

A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}formamide (0.67 g, 2.82 mmol) in anhydrous dichloromethane (20 ml) was cooled under argon in an ice-water bath before the addition of diisopropylamine (1.78 ml, 12.7 mmol) followed by phosphorus oxychloride (0.393 ml, 4.23 mmol). The reaction was stirred at between 2-5° C. for 2 hrs. The mixture was then reduced in vacuo and the residue treated with saturated aqueous sodium hydrogen carbonate (20 ml) and extracted with dichloromethane (20 ml). The organic layer was passed through a hydrophobic frit and the reduced in vacuo to give a yellow solid. Further drying in vacuo gave [2-chloro-3-(trifluoromethyl)phenyl]methyl isocyanide as an orange gum (0.66 g) which was used without further purification.

後処理

  1. extractionextracted with dichloromethane (20 ml)
  2. customto give a yellow solid
  3. customFurther drying in vacuo

出典と根拠

ORDレコード
ord-8a7f7324880e447caf60995de0fbbff2
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048907B2

反応ノート

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