Benzoyl chloride → HCID 15406406, compound

HRID 616629Notes

Reaction equation

HRID 616629 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[C:18]([C:8]1[S:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15422638HCID 15422638, compound

Product 1

HCID 15406406HCID 15406406, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 100 ml. of 1,2-dichloroethane were added 5.0 g. (0.021 mole) of 3-phenyl-6-methoxybenzothiophene and 2.81 g. (0.021 mole) of benzoyl chloride. The mixture was cooled to 0° C., and 2.93 g. (0.022 mole) of aluminum chloride were added. The mixture was stirred for one hour, and ice then was added. The resulting organic layer was separated, washed with water, and evaporated. To the residue were added 250 ml. of methanol and 10 ml. of 5N sodium hydroxide. The mixture was refluxed for 30 minutes, evaporated, and ether and water were added to the residue. The ether layer was separated, washed with 1N sodium hydroxide, 1N hydrochloric acid, and aqueous soidum chloride. The ether layer then was dried over magnesium sulfate, filtered, and evaporated. The residue was crystallized from methanol to obtain 3.77 g. (52 percent) of the title compound, m.p. 94°-95.5° C.

Workup

  1. additionice then was added
  2. customThe resulting organic layer was separated
  3. washwashed with water
  4. customevaporated
  5. additionTo the residue were added 250 ml
  6. temperatureThe mixture was refluxed for 30 minutes
  7. customevaporated
  8. additionether and water were added to the residue
  9. customThe ether layer was separated
  10. washwashed with 1N sodium hydroxide, 1N hydrochloric acid, and aqueous soidum chloride
  11. dry with materialThe ether layer then was dried over magnesium sulfate
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue was crystallized from methanol
  15. customto obtain 3.77 g

Sources & evidence

ORD record
ord-8cad5b6157cb43d79cbec7d1ab51a421
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

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