Pyridinium chloride → 7-Acetyl-4-hydroxybenzo[d]thiazol-2(3H)-one

HRID 749239Notes

Reaction equation

HRID 749239 reaction equation
[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([O:14]C)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.N1C=CC=CC=1>CN1CCCC1=O.O>[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 450769887-Acetyl-4-methoxybenzo[d]thiazol-2(3H)-one

Product 1

HCID 450769877-Acetyl-4-hydroxybenzo[d]thiazol-2(3H)-oneYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 7-acetyl4-methoxy-1,3-benzothiazol-2(3H)-one (1.2 g), pyridine hydrochloride (2.77 g), in dry 1-methyl-2-pyrrolidone(6 ml), was heated at 190° C. in a microwave reactor for 90 min. The reaction mixture was cooled to room temperature, and diluted with water. The precipitated solid was collected by filtration, washed with water and dried under vacuum at 40° C. to give the title compound (1.07 g). LCMS RT=2.46 min.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-fe87213bfd7e406bb29aebc33ee06b8e
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

Loading…