Bromine → 5-Fluoro-6-[1-(2,3,6-trichlorophenyl)ethoxy]-1,3-benzothiazol-2-amine

HRID 1929352Notes

Reaction equation

HRID 1929352 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=1[Cl:20])[CH3:11])[NH2:5].[S-:21][C:22]#[N:23].[K+].BrBr>>[F:1][C:2]1[C:8]([O:9][CH:10]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=2[Cl:20])[CH3:11])=[CH:7][C:6]2[S:21][C:22]([NH2:23])=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 685123003-Fluoro-4-[1-(2,3,6-trichlorophenyl)ethoxy]aniline

Product 1

HCID 866469505-Fluoro-6-[1-(2,3,6-trichlorophenyl)ethoxy]-1,3-benzothiazol-2-amineYield 74.7%

Procedure

5-Fluoro-6-[1-(2,3,6-trichlorophenyl)ethoxy]-1,3-benzothiazol-2-amine was prepared according to the method described in Example 20d but from 1.35 g of 3-fluoro-4-[1-(2,3,6-trichlorophenyl)ethoxy]aniline, 1.56 g of potassium thiocyanate and 0.207 cm3 of dibromine. We obtain 1.18 g of 5-fluoro-6-[1-(2,3,6-trichlorophenyl)ethoxy]-1,3-benzothiazol-2-amine in the form of an orange-coloured powder, which has the following characteristics:

Workup

  1. custom5-Fluoro-6-[1-(2,3,6-trichlorophenyl)ethoxy]-1,3-benzothiazol-2-amine was prepared

Sources & evidence

ORD record
ord-e92a7830fd134fb79855e2ff53766e50
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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