Potassium Iodide → Ethyl 2-[4-(5-chlorobenzothiazol-2-yl) methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]acetate

HRID 1682443Notes

Reaction equation

HRID 1682443 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH:3]1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Br[CH2:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:23]=2[N:24]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O>[Cl:29][C:26]1[CH:27]=[CH:28][C:22]2[S:21][C:20]([CH2:19][N:7]3[C:6]4[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=4[O:4][CH:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]3=[O:1])=[N:24][C:23]=2[CH:25]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15292312Ethyl (3-oxo-3,4-dihydro-2h-1,4-benzoxazine-2-yl)acetateHCID 152923132-(Bromomethyl)-5-chloro-1,3-benzothiazole

Product 1

HCID 15292314Ethyl 2-[4-(5-chlorobenzothiazol-2-yl) methyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 2-(3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]acetate (150 mg), 2-bromomethyl-5-chlorobenzothiazole (186 mg) and potassium iodide (13 mg) were dissolved in dimethyl sulfoxide (2 ml). Potassium carbonate (133 mg) was added and the mixture was stirred at room temperature for 15 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled away.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-3bee6e69b6374e498dbfb46ae3ead3c6
Source dataset
uspto-grants-1997_06
Patent number
US05635505

Reaction notes

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