Thionyl Chloride → 3-Chlorocarbonyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

HRID 485455Notes

Reaction equation

HRID 485455 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=[CH:16][C:3]1=2.S(Cl)([Cl:22])=O>>[Cl:22][C:17]([C:14]1[CH:15]=[CH:16][C:3]2[C:2](=[O:1])[CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[S:5][C:4]=2[CH:13]=1)=[O:19]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 8270515-oxo-6H-benzo[b][1]benzothiepine-2-carboxylic acid

Product 1

HCID 202702113-Chlorocarbonyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Procedure

Heat a solution of 5 g. of 10,11-dihydro-11-oxodibenzo[b,f]thiepin-3-carboxylic acid and 40 ml. of thionyl chloride under reflux for 20 minutes. Evaporate the reaction mixture under vacuum to dryness. Repeat the evaporation with two 30 ml. portions of carbon tetrachloride. Crystallize the residue from diisopropyl ether to obtain the title product.

Workup

  1. temperatureHeat a solution of 5 g
  2. customEvaporate the reaction mixture under vacuum to dryness
  3. customRepeat the evaporation with two 30 ml
  4. customCrystallize the residue from diisopropyl ether

Sources & evidence

ORD record
ord-637704ddc69f4fdd90fe66eab68e6054
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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