Bromine → 6-[1-(2,3-Dichloro-6-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-amine

HRID 1929350Notes

Reaction equation

HRID 1929350 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[F:20])[CH3:11].[S-:21][C:22]#[N:23].[K+].BrBr>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([F:20])=[CH:15][C:16]2[N:17]=[C:22]([NH2:23])[S:21][C:18]=2[CH:19]=1)[CH3:11]

Participants

4

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 68508931HCID 68508931, compound

Product 1

HCID 866469486-[1-(2,3-Dichloro-6-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-amineYield 97.5%

Procedure

6-[1-(2,3-Dichloro-6-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-amine was prepared according to the method described in Example 20d but from 2 g of 4-[1-(2,3-dichloro-6-fluorophenyl)ethoxy]-3-fluoroaniline, 2.44 g of potassium thiocyanate and 0.322 cm3 of dibromine. We obtain 2.3 g of 6-[1-(2,3-dichloro-6-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-amine in the form of a cream-coloured powder, which has the following characteristics:

Workup

  1. custom6-[1-(2,3-Dichloro-6-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-amine was prepared

Sources & evidence

ORD record
ord-79ff5b5cec7e4959b70272f6bf7a533f
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

Loading…