Hydrochloric Acid → 4-Phenoxy-1,3-benzothiazol-2(3H)-one

HRID 1164519Notes

Reaction equation

HRID 1164519 reaction equation
[O-:1]CC.[Na+].[Na].Br[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[N:11]=1.Cl>CC(C)=O.C(O)C>[O:1]=[C:7]1[NH:11][C:10]2[C:12]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:14]=[CH:15][C:9]=2[S:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 130970832-Bromo-4-phenoxybenzothiazole

Product 1

HCID 130970844-Phenoxy-1,3-benzothiazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

To a sodium ethoxide solution prepared with sodium metal (460 mg) and anhydrous ethanol (50 ml) was added 2-bromo-4-phenoxybenzothiazole (3.0 g). The mixture was refluxed with stirring 45 minutes. The solvent was removed under reduced pressure to give a residue, to which was added 10% hydrochloric acid (30 ml) and acetone (50 ml). The resultant mixture was refluxed with stirring for 2 hours. The solvent was removed under reduced pressure to give a residue, which was recrystallized from a mixture of ethanol and n-hexane to give crystalline 2-oxo-4-phenoxybenzothiazoline (2.0 g).

Workup

  1. temperatureThe mixture was refluxed
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue
  4. stirringwith stirring for 2 hours
  5. customThe solvent was removed under reduced pressure
  6. customto give a residue, which
  7. customwas recrystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-bc61fb038062442db0736a3e435a138a
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

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