1-Chloro-2,4-Dinitrobenzene → 5-Nitrobenzothiazole

HRID 1936591Notes

Reaction equation

HRID 1936591 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-])=O.CN(C)[CH:16]=[S:17].C(O)C>C1(C)C(C)=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[S:17][CH:16]=[N:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 702EthanolHCID 69794N,N-Dimethylthioformamide

Product 1

HCID 3501355-NitrobenzothiazoleYield 52.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 10 g of 1-chloro-2,4-dinitrobenzene and 20.26 g of N,N-dimethylthioformamide is heated to 60° C. for 3 hours. The resulting solid is suspended in 25 mL of xylene and the mixture is heated to reflux for 4 hours. The mixture is allowed to cool to room temperature and 15 mL of ethanol are added. The resulting suspension is filtered, and the brown solid is washed with a minimum amount of ethanol. The solid is dissolved in 120 mL of ethanol, heated to boiling, and filtered hot to remove trace solids. After reduction of the volume to about 100 mL, the solution is allowed to stand overnight at room temperature. The resulting solid is filtered and washed with ethanol to provide 4.68 g of 5-nitrobenzothiazole as reddish-brown needles.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 4 hours
  3. temperatureto cool to room temperature
  4. filtrationThe resulting suspension is filtered
  5. washthe brown solid is washed with a minimum amount of ethanol
  6. dissolutionThe solid is dissolved in 120 mL of ethanol
  7. temperatureheated
  8. filtrationfiltered hot
  9. customto remove trace solids
  10. filtrationThe resulting solid is filtered
  11. washwashed with ethanol

Sources & evidence

ORD record
ord-849ee39ab9014d209e4ff1b1834b17e5
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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