Potassium Iodide → 2-[(3-Nitrophenoxy)methyl]-1,3-benzothiazole

HRID 1981952Notes

Reaction equation

HRID 1981952 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[N+:12]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)=O>[S:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][O:21][C:17]1[CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 3049782-(Chloromethyl)benzothiazole

Product 1

HCID 136311552-[(3-Nitrophenoxy)methyl]-1,3-benzothiazoleYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-chloromethylbenzthiazole (17.6 g), 3-nitrophenol (13.2 g), cesium carbonate (30 g), sodium carbonate (10 g), potassium iodide (0.5 g) and acetone (600 ml) is heated at reflux overnight. The mixture is filtered and the resulting solution is partially concentrated. A crystalline solid forms which is filtered and dried giving 22.8 g (84% yield) m.p. 156°-157° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture is filtered
  4. concentrationthe resulting solution is partially concentrated
  5. filtrationA crystalline solid forms which is filtered
  6. customdried
  7. customgiving 22.8 g (84% yield) m.p. 156°-157° C.

Sources & evidence

ORD record
ord-2395910997d640bb901f690a72ccfbe7
Source dataset
uspto-grants-1986_06
Patent number
US04594425

Reaction notes

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