2-Chloro-6-nitrobenzothiazole → 4-(6-Nitrobenzothiazol-2-yl)piperazine-1-carboxylic acid benzyl ester

HRID 1783495Notes

Reaction equation

HRID 1783495 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.[N:14]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])(O)=O.[Na+]>CCO>[CH2:23]([O:22][C:20]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:16][CH2:15]1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 754762-Chloro-6-nitrobenzothiazoleHCID 516892Sodium BicarbonateHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 150278014-(6-Nitrobenzothiazol-2-yl)piperazine-1-carboxylic acid benzyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-6-nitrobenzothiazole (1.00 g, 4.66 mmol), benzyl 1-piperazinecarboxylate (1.03 g, 4.66 mmol), and NaHCO3 (0.783 g, 9.32 mmol) in EtOH was heated at reflux temperature for 2 h, concentrated, and extracted with EtOAc. The combined extracts were dried over Na2SO4 and concentrated in vacuo to provide the title compound (1.13 g, 61%), characterized by NMR and mass spectral analyses.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. concentrationconcentrated
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ce445fe55a1405e8ec597df0c6fc1cc
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

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