2,4-Dichloroaniline → 4,6-Dichloro-1,3-benzothiazol-2(3H)-imine

HRID 1419715Notes

Reaction equation

HRID 1419715 reaction equation
BrBr.[Cl:3][C:4]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=1[NH2:6].[S-:12][C:13]#[N:14].[Na+]>C(O)(=O)C>[NH2:14][C:13]1[S:12][C:7]2[CH:8]=[C:9]([Cl:11])[CH:10]=[C:4]([Cl:3])[C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 111232,4-DichloroanilineHCID 24408BromineHCID 516871Sodium thiocyanate

Product 1

HCID 1127224,6-Dichloro-1,3-benzothiazol-2(3H)-imine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

197 g (1.23 mol) of bromine were slowly added dropwise, while cooling with ice, to a solution of 200 g (1.23 mol) of 2,4-dichloroaniline and 200 g (2.46 mol) of sodium thiocyanate in 1.5 1 of glacial acetic acid. Stirring was carried out for 16 hours at about 20° C., after which the solid was separated off and washed with 10% strength sodium hydroxide solution and water.

Workup

  1. customafter which the solid was separated off
  2. washwashed with 10% strength sodium hydroxide solution and water

Sources & evidence

ORD record
ord-0ccdfe601ca34f66adb31452192eb659
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

Loading…