Bromine → 4-Fluoro-1,3-benzothiazol-2-amine

HRID 57225Notes

Reaction equation

HRID 57225 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH2:11])=[S:10].BrBr>C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]2[N:8]=[C:9]([NH2:11])[S:10][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 2737500(2-Fluorophenyl)thiourea

Product 1

HCID 20498874-Fluoro-1,3-benzothiazol-2-amineYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of (2-fluorophenyl)thiourea (1.7 g, 10.0 mmol) in chloroform (25 ml) was added a solution of bromine (0.51 mL; 10.0 mmol) dropwise at room temperature. The resulting mixture was heated under reflux for 3 hrs. The solvent was evaporated, water was added and the mixture was neutralized with ammonium hydroxide. The resulting white precipitation was collected by filtration and dried to yield 1.2 g (72%) of the title compound which was used in the subsequent step without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. customThe solvent was evaporated
  4. additionwater was added
  5. customThe resulting white precipitation
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-5df27968bd9a4728ae9794b53551ce5b
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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