Potassium Carbonate → HCID 11118300, compound

HRID 1281866Notes

Reaction equation

HRID 1281866 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:15]([CH3:16])=[C:14]([CH3:17])[S:13][C:12]=1Br)=[O:10].C(=O)([O-])[O-].[K+].[K+].O.C(OCC)(=O)C>CS(C)=O>[CH3:17][C:14]1[S:13][C:12]2[O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[NH:8][C:9](=[O:10])[C:11]=2[C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11823569HCID 11823569, compoundHCID 22728543Water ethylacetate

Product 1

HCID 11118300HCID 11118300, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
165 °C

Procedure

To a solution of N-(2-hydroxyphenyl)-2-bromo-4,5-dimethyl-3-thiophenecarboxamide (3.3 g) in dimethyl sulfoxide (50 ml) was added potassium carbonate (2.8 g) and the mixture was stirred at 160-170° C. for 20 minutes. The reaction system was cooled to room temperature and the reaction mixture was poured into water-ethyl acetate. The insoluble matter was filtrated and the filtrate was extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 2,3-dimethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.4 g).

Workup

  1. temperatureThe reaction system was cooled to room temperature
  2. filtrationThe insoluble matter was filtrated
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-635b734c672b487e9d92a8150d9b9405
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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