2-Chlorobenzothiazole → N2-(4-bromo-2-fluorophenyl)-1,3-benzothiazol-2-amine

HRID 897670Notes

Reaction equation

HRID 897670 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.Cl[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]2[S:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 119872-ChlorobenzothiazoleHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 21985682N2-(4-bromo-2-fluorophenyl)-1,3-benzothiazol-2-amineYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 4-bromo-2-fluoroaniline (1.00 g, 5.26 mmol) in toluene (25 mL) was added 2-chlorobenzothiazole (0.75 mL, 5.79 mmol). The purple solution was heated at 110-150° C. in a resealable tube for 66 hand then cooled to room temperature. The resulting brown solution was concentrated to give a purple solid which was triturated with heptane to afford N2-(4-bromo-2-fluorophenyl)-1,3-benzothiazol-2-amine (1.699 g, 99%) as a light purple powder. RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) tr=13.82 min, 95%; m/z 325 (MH+).

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationThe resulting brown solution was concentrated
  3. customto give a purple solid which
  4. customwas triturated with heptane

Sources & evidence

ORD record
ord-e5902fb788df46eca0abe32020c9ae48
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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