Hydrochloric Acid → HCID 10923302, compound

HRID 1281895Notes

Reaction equation

HRID 1281895 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][C:11]([C:13]1[CH:17]=[C:16]([CH3:18])[S:15][C:14]=1Br)=[O:12].C[O-].[Na+].O.Cl>CN(C)C=O>[CH3:18][C:16]1[S:15][C:14]2[O:1][C:2]3[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=3[NH:10][C:11](=[O:12])[C:13]=2[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10914818HCID 10914818, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10923302HCID 10923302, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-hydroxy-3-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (2.30 g) and sodium methoxide (549 mg) in N,N-dimethylformamide (12 ml) was stirred under reflux with heating for 19 hours. The reaction system was cooled to room temperature, and the reaction mixture was poured into water (50 ml). The mixture was neutralized with hydrochloric acid, extracted twice with chloroform and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent hexane:ethyl acetate=1:1) to give 2-methyl-9-methoxythieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.87 g).

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 19 hours
  3. extractionextracted twice with chloroform
  4. washwashed with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-21f2cf923ea649d3bac20a16985c670a
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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