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

HRID 653176Notes

Reaction equation

HRID 653176 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-chloromethylbenzothiazole (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-62637598987f46eb91afabe5ed399682
Source dataset
uspto-grants-1987_06
Patent number
US04675405

Reaction notes

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