N,N,N',N'-Tetramethylethylenediamine → 2-(Dicyclohexylphosphanyl)-1-(2,4,6-trimethylphenyl)-1H-imidazole

HRID 732877

反応式

HRID 732877 の反応式
CN(CCN(C)C)C.[C:9]1([CH3:22])[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.C([Li])CCC.[CH:28]1([P:34]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)Cl)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CCCCCC.O>[C:9]1([CH3:22])[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[P:34]([CH:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1)[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

参加物

7

反応物 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2734135ChlorodicyclohexylphosphineHCID 98154601-Mesityl-1h-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 534118192-(Dicyclohexylphosphanyl)-1-(2,4,6-trimethylphenyl)-1H-imidazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8058Hexane溶媒2 回

実験手順

1.6 ml of TMEDA (15 mmol.) are added to a suspension of 1.86 g (10 mmol.) of N-mesitylimidazole in 30 ml of hexane. 6.25 ml of 1.6 molar n-butyllithium solution (10 mmol.) are added at room temperature. The mixture is then heated for 2.5 hours at reflux temperature (solution 1). In another flask, 2.2 ml (10 mmol.) of dicyclohexylchlorophosphane are mixed with 20 ml of hexane and heated to 60° C. (solution 2). The boiling solution 1 is then slowly transferred into solution 2, which is at 60° C., by means of a cannula. The mixture is then boiled for a further 1 hour at reflux, the solution is cooled, and 20 ml of degassed water are added thereto. The organic phase is filtered off over magnesium sulfate. The solution is concentrated in vacua; 30 ml of pentane are added thereto, and the mixture is boiled for 1 hour at reflux. The product precipitates in crystalline form at −30° C. and is filtered off while cold. Yield: 2.48 g (65%)

後処理

  1. temperatureThe mixture is then heated for 2.5 hours
  2. customis at 60° C., by means of a cannula
  3. temperatureat reflux
  4. temperaturethe solution is cooled
  5. filtrationThe organic phase is filtered off over magnesium sulfate
  6. concentrationThe solution is concentrated in vacua
  7. addition30 ml of pentane are added
  8. waitthe mixture is boiled for 1 hour
  9. temperatureat reflux
  10. customThe product precipitates in crystalline form at −30° C.
  11. filtrationis filtered off while cold

出典と根拠

ORDレコード
ord-4e99e6c803a0495f911d811494d36ce0
出典データセット
uspto-grants-2009_09
特許番号
US07589081B2

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