Potassium Carbonate → HCID 11054588, compound

HRID 1281869Notes

Reaction equation

HRID 1281869 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2Br)=[O:11])[C:5]([OH:8])=[CH:6][CH:7]=1.[C:18](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:13]3[S:14][C:15]([CH3:18])=[CH:16][C:12]=3[C:10](=[O:11])[NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18422151HCID 18422151, compound

Product 1

HCID 11054588HCID 11054588, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of N-(3-chloro-6-hydroxyphenyl)-2-bromo-3-thiophenecarboxamide (4.1 g) in dimethyl sulfoxide (33 ml) was added potassium carbonate (3.3 g), and the mixture was stirred at 140-150° C. for 75 minutes. The reaction system was cooled to room temperature and the reaction mixture was poured into ice water. The precipitated crystals were collected by filtration. The filtrate was extracted twice with chloroform, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue and the above-mentioned crystals were combined and purified by silica gel column chromatography (chloroform:methanol=20:1, hexane:ethyl acetate=1:1-ethyl acetate:methanol=20:1). The obtained solid was collected by filtration from hexane-ethyl acetate to give 7-chloro-2-methylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (660 mg).

Workup

  1. temperatureThe reaction system was cooled to room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. extractionThe filtrate was extracted twice with chloroform
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. custompurified by silica gel column chromatography (chloroform:methanol=20:1, hexane:ethyl acetate=1:1-ethyl acetate:methanol=20:1)
  7. filtrationThe obtained solid was collected by filtration from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1de34f6b05844a5e8b58d61d98507450
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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