Hydrochloric Acid → N-(4-(4-(Ethylheptylamino)butyl)phenyl)methanesulfonamide

HRID 466362

反応式

HRID 466362 の反応式
[CH2:1]([N:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:4](=O)[CH2:5][CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH3:2].CC1C=C(C(=O)C)C=CC=1NS(C)(=O)=O.CSC.B.C(Cl)Cl.Cl>C1COCC1.CCO.CO>[CH2:1]([N:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:12][CH:13]=1)[CH3:2]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 14891420N-Ethyl-n-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamideHCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamide

生成物 1

HCID 9864094N-(4-(4-(Ethylheptylamino)butyl)phenyl)methanesulfonamide

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide as prepared in Preparation 3 (2.0 g, 0.005 mol) in THF (20 ml), under N2, is treated during 1 hour with a 1M solution of borane dimethylsulfide in CH2Cl2 (15.8 ml, 0.0158 mol). The mixture is kept at ambient temperature for 30 minutes and at reflux for 4 hours. It is then cooled in an ice bath and treated slowly with MeOH (2 ml). This mixture is kept at ambient temperature for 18 hours, acidified with a solution of HCl in EtOH and refluxed for 1 hour. The cooled solution is concentrated and the residue is mixed with saturated NaHCO3 and extracted with CH2Cl2. The extracts are washed with brine, dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (350 g) with 5% MeOH-0.5% NH4OH--CH2Cl2. The N-[4-[4 -(ethylheptylamino)butyl]phenyl]methanesulfonamide thus obtained is mixed with saturated NaHCO3 and extracted with Et2O. The extracts are washed with brine, dried (MgSO4) and concentrated. A solution of the residue in pentane is filtered through Magnisol and concentrated. MS: theory for C20H36N2O2S(M+): 368.2497. Found: 368.2498.

後処理

  1. temperatureat reflux for 4 hours
  2. temperatureIt is then cooled in an ice bath
  3. waitThis mixture is kept at ambient temperature for 18 hours
  4. temperaturerefluxed for 1 hour
  5. concentrationThe cooled solution is concentrated
  6. additionthe residue is mixed with saturated NaHCO3
  7. extractionextracted with CH2Cl2
  8. washThe extracts are washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customThe residue is chromatographed on silica gel (350 g) with 5% MeOH-0.5% NH4OH--CH2Cl2

出典と根拠

ORDレコード
ord-2995cb731ad84016ba70e90dafb70e97
出典データセット
uspto-grants-1992_10
特許番号
US05155268

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