Hydrochloric Acid → 2-Chlorobenzo[d]thiazol-6-ol

HRID 549676Notes

Reaction equation

HRID 549676 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C[O:6][C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([Cl:14])[S:13][C:9]=2[CH:8]=1.Cl>C1(C)C=CC=CC=1>[Cl:14][C:12]1[S:13][C:9]2[CH:8]=[C:7]([OH:6])[CH:16]=[CH:15][C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 147498432-Chlorobenzo[d]thiazol-6-olYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Aluminum chloride (1.98 g, 14.9 mmol) was added to a solution of 6-methoxy-2-chlorobenzothiazole (1.06 g, 5.31 mmol) in toluene (40 mL), and the reaction mixture was heated to 110° C. After 1 h, the reaction mixture was allowed to cool to rt and 1 M aqueous HCl (40 mL) was added. The resulting precipitate was collected by filtration and washed with water (2×), saturated aqueous NaHCO3 (2×) and water (2×). The solid was air-dried, yielding 0.800 g (81%) of the title compound as a brown solid. LC-MS: RT=7.18 min., [M+H]+=185.9.

Workup

  1. temperatureto cool to rt
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water (2×), saturated aqueous NaHCO3 (2×) and water (2×)
  4. customThe solid was air-dried

Sources & evidence

ORD record
ord-ce4f2e0990ab4c64a77bedb5fe934984
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Reaction notes

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