Thionyl Chloride → 2-Chlorocarbonyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

HRID 894192Notes

Reaction equation

HRID 894192 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=O)=[CH:16][C:3]1=2.S(Cl)([Cl:22])=O>>[Cl:22][C:17]([C:15]1[CH:14]=[CH:13][C:4]2[O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[C:3]=2[CH:16]=1)=[O:19]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12446821Olopatadine Impurity 17

Product 1

HCID 134560052-Chlorocarbonyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Procedure

Heat a solution of 5 gm. of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-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 gm
  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-03917c48796442249d1cb806af3c04d1
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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