Water → HCID 11096442, compound

HRID 1281863Notes

Reaction equation

HRID 1281863 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[CH:15]=[C:14]([CH3:16])[S:13][C:12]=1Br)=[O:10].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:16][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[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 11088245HCID 11088245, compound

Product 1

HCID 11096442HCID 11096442, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of N-(2-hydroxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (15 g) in dimethyl sulfoxide (100 ml) was added potassium carbonate (13 g), and the mixture was stirred at 140° C. for 1.5 hours. The reaction system was cooled to room temperature and the reaction mixture was poured into water (800 ml). After neutralization with hydrochloric acid, the mixture was extracted twice with chloroform and washed with water and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. To the residue was added chloroform and the crystals were collected by filtration to give 2-methylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (3.3 g).

Workup

  1. temperatureThe reaction system was cooled to room temperature
  2. extractionAfter neutralization with hydrochloric acid, the mixture was extracted twice with chloroform
  3. washwashed with water and saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionTo the residue was added chloroform
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-ab31dc9939834a229a468a8a92e82dbf
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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