HCID 54311892, compound → HCID 12687104, compound

HRID 903652Notes

Reaction equation

HRID 903652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:3]=1[CH2:17][C:18]([OH:20])=O>O>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]2[S:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[CH2:17][C:18](=[O:20])[C:14]=2[CH:13]=1

Participants

3

Reactant 1

HCID 54311892HCID 54311892, compound

Product 1

HCID 12687104HCID 12687104, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 30 g of 2-chloro-6-(p-methoxyphenylthio)-phenylacetic acid and 300 g of polyphosphoric acid was stirred at 110° C. for 3 hours. After cooling, to the mixture was added water and the mixture was extracted with chloroform. The extract was washed with 1 N sodium hydroxide solution, saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to afford 22.9 g (81%) of 2-methoxy-9-chloro-10,11-dihydrodibenzo[b,f]thiepin-11-one as reddish crystals having a melting point of 117°-120° C.

Workup

  1. temperatureAfter cooling, to the mixture
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with 1 N sodium hydroxide solution, saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-376cf5090dbb4404bf777d6ae5267dc0
Source dataset
uspto-grants-1980_10
Patent number
US04228284

Reaction notes

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