p-Fluoronitrobenzene → HCID 16736005, compound

HRID 1373114Notes

Reaction equation

HRID 1373114 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 187201N-BOC-ethylenediamine

Product 1

HCID 16736005HCID 16736005, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

4.2 g (29.7 mmol) of N-tert.butoxycarbonyl-ethylenediamine, 5.0 g (31.2 mmol) of 4-fluoro-nitrobenzene and 7.0 g (50.6 mmol) of potassium carbonate are stirred in 25 ml of DMSO for 9 hours at 60° C. After cooling the mixture is diluted with water and extracted with ethyl acetate. The combined organic extracts are dried and evaporated down. The residue is stirred with petroleum ether, decanted off and evaporated down again. The product is stirred with ether and suction filtered.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts are dried
  4. customevaporated down
  5. customdecanted off
  6. customevaporated down again
  7. stirringThe product is stirred with ether and suction
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5a7c8b32f71f419db4b0ef13e6f652a8
Source dataset
uspto-grants-2007_01
Patent number
US07160901B2

Reaction notes

Loading…