Formic Acid → 5-Methoxybenzothiazole

HRID 1750091Notes

Reaction equation

HRID 1750091 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[SH:11].B(O)(O)O.[CH:16](O)=O>O>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:4]2[S:11][CH:16]=[N:2][C:3]=2[CH:8]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7628Boric AcidHCID 121992962-Amino-4-methoxybenzene-1-thiol hydrochloride

Product 1

HCID 124222005-MethoxybenzothiazoleYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of intermediate 23 (1.33 g, 6.9 mmol), boric acid (2.3 g, 37.2 mmol) and formic acid (17 mL) was heated to reflux and stirred for 6 h. The reaction mixture was cooled to rt and diluted with water. The solution was made alkaline and extracted with ethyl acetate. Further purification by column chromatography (elution with PE/EtOAc=3:1) gave 5-methoxybenzo[d]thiazole (intermediate 24) (290 mg, 15%). HPLC: 99%, RI 2.646 min. MS (ESI) m/z 166.0 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. extractionextracted with ethyl acetate
  4. customFurther purification
  5. washby column chromatography (elution with PE/EtOAc=3:1)

Sources & evidence

ORD record
ord-f43dd5eb9df443c89c4037bbad7a0720
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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