4-Chloro-1,2-dinitrobenzene → HCID 3107057, compound

HRID 1081471Notes

Reaction equation

HRID 1081471 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.N[N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:3]=1

Participants

4

Reactant 2

HCID 330974-Chloro-1,2-dinitrobenzeneHCID 813491-Amino-4-methylpiperazine

Product 1

HCID 3107057HCID 3107057, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 35 g of 4-chloro-1,2-dinitrobenzene and 20 g of 1-amino-4-methylpiperazine in 200 ml of 96° EtOH is stirred for 24 hours at RT. The reaction mixture is evaporated under vacuum and the residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent to give 17.5 g of the expected product after crystallization from an iso ether/heptane mixture (50/50; v/v). M.p.=108° C.

Workup

  1. customThe reaction mixture is evaporated under vacuum
  2. customthe residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent

Sources & evidence

ORD record
ord-b073ac6c8d6142bf9b89cd4f89c701ec
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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