2-Bromo-5-nitroaniline → HCID 178526506, compound

HRID 1791935Notes

Reaction equation

HRID 1791935 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(O[C:15]([S-:17])=[S:16])C.[K+]>CN1CCCC1=O>[SH:17][C:15]1[S:16][C:2]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=2[N:4]=1

Participants

4

Reactant 2

HCID 826072-Bromo-5-nitroanilineHCID 2735045Potassium ethylxanthate

Product 1

HCID 178526506HCID 178526506, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

2-Bromo-5-nitroaniline (10 g) was dissolved in N-methyl-2-pyrrolidone (50 mL), and potassium ethylxanthate (14.8 g) was added thereto. The mixture was stirred at 140° C. with heating. The reaction mixture was concentrated under reduced pressure, and water (300 mL) and conc. hydrochloric acid (10 mL) were added to the residue. The precipitated solid was collected by filtration, which was then dissolved in 1 mol/L aqueous sodium hydroxide solution (80 mL). After washing with chloroform, 1 mol/L hydrochloric acid was added thereto, and the precipitated solid was collected by filtration to give 2-mercapto-5-nitrobenzothiazole (8.43 g) as an orange powder.

Workup

  1. temperaturewith heating
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water (300 mL) and conc. hydrochloric acid (10 mL)
  3. additionwere added to the residue
  4. filtrationThe precipitated solid was collected by filtration, which
  5. dissolutionwas then dissolved in 1 mol/L aqueous sodium hydroxide solution (80 mL)
  6. washAfter washing with chloroform, 1 mol/L hydrochloric acid
  7. additionwas added
  8. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ca9eb8ff3b4e49cd9faf6813ffe9e145
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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