Ammonium Hydroxide → 6-Bromo-2-chlorobenzothiazole

HRID 1850029Notes

Reaction equation

HRID 1850029 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=O)[S:8][C:4]=2[CH:3]=1.[NH4+].[OH-].O=P(Cl)(Cl)[Cl:16]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([Cl:16])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 1884446-Bromo-2,3-dihydro-1,3-benzothiazol-2-one

Product 1

HCID 20498716-Bromo-2-chlorobenzothiazoleYield 83%

Procedure

A solution of 6-bromobenzothiazolin-2-one (500 mg, 2.2 mmol) in POCl3 (5 mL) was refluxed during 18 h, then poured onto ice. The solution was neutralized to pH 9 by addition of NH4OH, and the resulting solid collected by filtration. Washing with water and drying in vacuo gave 6-bromo-2-chlorobenzothiazole (450 mg, 83%).

Workup

  1. additionpoured onto ice
  2. filtrationthe resulting solid collected by filtration
  3. washWashing with water
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-f2a39a62e9a74d96a2aa6f0eb61867b1
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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