Hydrogen iodide → 5-Benzothiazolol

HRID 1750092Notes

Reaction equation

HRID 1750092 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][CH:9]=[N:8][C:7]=2[CH:11]=1.I>O>[S:10]1[C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:11][C:7]=2[N:8]=[CH:9]1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 124222005-Methoxybenzothiazole

Product 1

HCID 35965065-BenzothiazololYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of intermediate 24 (272 mg, 1.65 mmol) and hydroiodic acid (45%, 2 mL) was heated to reflux for 5 h. The mixture was diluted with water and filtered. The filtrate was neutralized and the solids were filtered, washed with water, and combined to give benzo[d]thiazol-5-ol (intermediate 25) (206 mg, 83%). HPLC: 99%, RT 2.038 min. MS (ESI) m/z 152.1 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. filtrationfiltered
  4. filtrationthe solids were filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-519ee086812f4c4b9d536035960bc5f4
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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