Thionyl Chloride → HCID 12962150, compound

HRID 1156280Notes

Reaction equation

HRID 1156280 reaction equation
O[CH: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]([O:17][CH3:18])=[CH:16][C:3]1=2.S(Cl)([Cl:21])=O>CCOCC>[Cl:21][CH: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]([O:17][CH3:18])=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4003528HCID 4003528, compound

Product 1

HCID 12962150HCID 12962150, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

11-Hydroxy-2-methoxy-6,11-dihydrodibenz[b,e]oxepin (13.85 g, 0.057 mole) is dissolved in anhydrous ether (180 ml) and cooled to 5° C. under a dry nitrogen atmosphere. Thionyl chloride (7.37 g; 0.062 mole) in ether (20 ml) is added dropwise while maintaining the temperature below 5° C. (Near the end of the addition a solid precipitates from the solution). The reaction is stirred at ambient temperature for 3 hours and filtered. The filtrate is removed in vacuo to give a solid which is combined with the filtered solid and recrystallized from cyclohexane to provide 10.5 g (70%) of crystals of 11-chloro-2-methoxy-6,11-dihydrodibenz[b,e]oxepin, m.p. 133°-134.5° C.

Workup

  1. temperaturewhile maintaining the temperature below 5° C. (
  2. additionNear the end of the addition a solid
  3. customprecipitates from the solution)
  4. filtrationfiltered
  5. customThe filtrate is removed in vacuo
  6. customto give a solid which
  7. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-bebe2666eb6d4ad2a56bca0c3284557d
Source dataset
uspto-grants-1982_06
Patent number
US04335122

Reaction notes

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