6-Methoxy-2-methylbenzothiazole → 2-Methyl-1,3-benzothiazol-6-ol

HRID 1290006Notes

Reaction equation

HRID 1290006 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[S:9][C:5]=2[CH:4]=1>Br.C(O)(=O)C>[OH:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[S:9][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 762546-Methoxy-2-methylbenzothiazole

Product 1

HCID 7593042-Methyl-1,3-benzothiazol-6-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-methoxy-2-methyl-benzothiazole (2.5 gm, 0.014 mol) in 30% HBr in acetic acid (15 mL) was stirred for 2 days at 70° C. After cooling, the solid was filtered, washed with ether, and dried in vacuo. The solid was taken up in water (20 mL) and neutralized with saturated NaHCO3 solution. The resulting solid was filtered, washed with water, and dried in vacuo at 40° C.; yield 1.2 gm.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered
  3. washwashed with ether
  4. customdried in vacuo
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-e78d533e30954659a804f54bf0544aa9
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

Loading…