Piperazine → 6-Nitro-2-piperazin-1-yl-1,3-benzothiazole

HRID 33152Notes

Reaction equation

HRID 33152 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C>O1CCCC1>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[S:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 754762-Chloro-6-nitrobenzothiazole

Product 1

HCID 7660126-Nitro-2-piperazin-1-yl-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1.40 mmol 2-chloro-6-nitrobenzothiazole (CA=[2407-11-6]), 4.19 mmol of piperazine and 4.19 mmol of triethylamine in 5 ml of tetrahydrofuran in a sealed tube was heated at 160° C. for 10 min under microwave irradiation. The reaction mixture was concentrated, and the residue was purified by chromatography (SiO2, methanol/dichloromethane) to yield the title compound as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (SiO2, methanol/dichloromethane)

Sources & evidence

ORD record
ord-770bc5918640493593aa98c45636360b
Source dataset
uspto-grants-2008_09
Patent number
US07429585B2

Reaction notes

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