Benzoyl chloride, 3-chloro- → HCID 20368321, compound

HRID 616637Notes

Reaction equation

HRID 616637 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.[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([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:23]

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 6451240Aluminum(III) ChlorideHCID 15422638HCID 15422638, compound

Product 1

HCID 20368321HCID 20368321, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 200 ml. of 1,2-dichloroethane were added 10.0 g. (0.042 mole) of 3-phenyl-6-methoxybenzothiophene and 6.5 g. (0.042 mole) of 3-chlorobenzoyl chloride. The mixture was stirred and cooled to 0° C., and 5.73 g. (0.042 mole) of aluminum chloride were added. The mixture was stirred for about one hour and ice then was added. The resulting organic layer was separated from the aqueous. The aqueous layer was washed with chloroform, and the chloroform was separated and added to the organic layer. The organic layer then was evaporated, and to the resulting residue were added 250 ml. of methanol and 15 ml. of 5N sodium hydroxide. The mixture was refluxed for 30 minutes and evaporated. The residue was recrystallized from methanol to obtain the title compound, m.p. 105° C.

Workup

  1. stirringThe mixture was stirred for about one hour
  2. additionice then was added
  3. customThe resulting organic layer was separated from the aqueous
  4. washThe aqueous layer was washed with chloroform
  5. customthe chloroform was separated
  6. additionadded to the organic layer
  7. customThe organic layer then was evaporated
  8. additionto the resulting residue were added 250 ml
  9. temperatureThe mixture was refluxed for 30 minutes
  10. customevaporated
  11. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-a28d64416f574db4884450a520c8a978
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

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