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

HRID 1075015Notes

Reaction equation

HRID 1075015 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-2af09a19d91e4b68a46aad7a9be70990
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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