Potassium Carbonate → HCID 11054588, compound

HRID 649994Notes

Reaction equation

HRID 649994 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

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

Sources & evidence

ORD record
ord-c558533cbd35451ea14ace4cf33c9c36
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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