N,N-dimethyl-p-phenylenediamine → N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamine

HRID 1457599ノート

反応式

HRID 1457599 の反応式
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 8130HeptanalHCID 516892Sodium BicarbonateHCID 2724942Triacetoxyborohydride

生成物 1

HCID 22099398N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamine収率 46.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3.50 g of N,N-dimethyl-p-phenylenediamine, 4.592 g of heptanal, 9.095 g of triacetoxyborohydride, 1.841 g of acetic acid and 257 ml of dichloromethane was stirred at room temperature for one hour. A saturated sodium hydrogen carbonate solution is added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue obtained was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1) to give 2.819 g of N,N-dimethyl-N'-heptyl-p-phenylenediamine (yield: 39%, oily product, IR (film): 3375, 2927, 1519 cm-1).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-a456221f39354a91800f7687886e9831
出典データセット
uspto-grants-1998_12
特許番号
US05849732

反応ノート

読み込み中…