2,3-Dichloroaniline → 2-amino-4,5-dichlorobenzothiazole

HRID 1882881Notes

Reaction equation

HRID 1882881 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[S-:10][C:11]#[N:12].[K+].BrBr>C(O)(=O)C>[NH2:12][C:11]1[S:10][C:5]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[C:3]=2[N:4]=1

Participants

5

Reactant 3

HCID 118442,3-DichloroanilineHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 6677392-amino-4,5-dichlorobenzothiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,3-dichloroaniline (1.0 g; 6.17 mmol) in glacial acetic acid (30 ml) was added potassium thiocyanate (3.6 g; 37 mmol) and the mixture was stirred at ambient temperature until a clear solution had formed. Bromine (0.48 ml; 9.26 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for five hours. The solvent was removed under reduced pressure and the residue was diluted with water and rendered alkaline by addition of aqueous sodium hydroxide (6M). The product was filtered off, washed with water and dried to yield the desired product quantitatively.

Workup

  1. customhad formed
  2. stirringthe reaction mixture was stirred at ambient temperature for five hours
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was diluted with water
  5. additionby addition of aqueous sodium hydroxide (6M)
  6. filtrationThe product was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-9760a974e5f24c6b88d727b803e4bba9
Source dataset
uspto-grants-2004_07
Patent number
US06759422B2

Reaction notes

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