P-Toluenesulfonamide → N,N-ditetradecyl-p-toluenesulfonamide

HRID 1596155ノート

反応式

HRID 1596155 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CN(C)C=O.CCOCC>[CH2:19]([N:17]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[S:14]([C:11]1[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][CH:12]=1)(=[O:16])=[O:15])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

参加物

6

反応物 3

HCID 6269P-ToluenesulfonamideHCID 8208Myristyl bromideHCID 11430Potassium Carbonate

生成物 1

HCID 21701141N,N-ditetradecyl-p-toluenesulfonamide収率 96.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (20.18 g; 146.00 mmol) is added to a solution of p-toluenesulfonamide (5.00 g; 29.20 mmol) and 1-bromotetradecane (21.70 ml; 73.00 mmol) in dimethylformamide (75 ml). The suspension is stirred for 20 h at reflux; the reaction medium is then cooled to room temperature, diluted with ether (100 ml) and filtered. The filtrate is washed with water (50 ml) and the aqueous phase is extracted with ether (100 ml). The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure to give a white solid which is purified by chromatography on a column of silica gel (eluent: 40/60 dichloromethane/hexane) to give N,N-ditetradecyl-p-toluenesulfonamide (15.86 g; 96%) in the form of a white solid.

後処理

  1. temperatureat reflux
  2. filtrationfiltered
  3. washThe filtrate is washed with water (50 ml)
  4. extractionthe aqueous phase is extracted with ether (100 ml)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a white solid which
  9. customis purified by chromatography on a column of silica gel (eluent: 40/60 dichloromethane/hexane)

出典と根拠

ORDレコード
ord-e9ffb329126746eb888dd0d9a9fb51c5
出典データセット
uspto-grants-2001_09
特許番号
US06291423B1

反応ノート

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