HCID 54311892, compound → HCID 12687104, compound

HRID 866934Notes

Reaction equation

HRID 866934 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%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 30g 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 1N sodium hydroxide solution, saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to afford 22.9g (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 1N sodium hydroxide solution, saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-b6a56b74a01442c79f8528217aab59c1
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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