Ethanol → HCID 15231558, compound

HRID 2258538Notes

Reaction equation

HRID 2258538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([N+:11]([O-])=O)[CH:3]=1.[CH:14]1(N)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C[CH2:23][OH:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:23](=[O:24])[N:11]([CH:14]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2899CycloheptylamineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 15231558HCID 15231558, compound

Procedure

A mixture of 18.2 g of 4-chloro-1,2-dinitrobenzene and 31 g of cycloheptylamine in 55 ml of 95% EtOH is left stirring for 15 hours at RT. The reaction mixture is concentrated under vacuum, the residue is extracted with EtOAc, washed with 1N HCl solution, with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with petroleum ether. 13 g of the expected product are obtained after crystallization from isopropanol.

Workup

  1. waitis left
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionthe residue is extracted with EtOAc
  4. washwashed with 1N HCl solution, with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica
  8. washeluting with petroleum ether

Sources & evidence

ORD record
ord-038ff05336af4badbd5c5392bcda08e6
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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