Sodium Hydroxide → HCID 22753277, compound

HRID 2163322Notes

Reaction equation

HRID 2163322 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[CH:29]=2)=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCCCl>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[C:29]=2[C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:17][CH:16]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 65042284-(2-Pyrrolidin-1-yl-ethoxy)-benzoic acidHCID 13527233HCID 13527233, compound

Product 1

HCID 22753277HCID 22753277, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The hydrochloride salt of 4-(2-pyrrolidinoethoxy)benzoic acid (7.77 grams; 0.028 mole) was converted to its corresponding acid chloride. To the acid chloride then were added 7.0 grams (0.028 mole) of the above benzothiophene and 250 ml. of 1,2-dichloroethane. A white suspension resulted. The mixture was cooled to b 0° to 10° C. and was treated gradually with 7.6 grams (0.57 mole) of aluminum chloride, giving rise to a brownish-yellow solution. The mixture was stirred at 0°-25° C. overnight, and then was poured over a mixture of 200 ml. of ice and 75 ml. of 5N sodium hydroxide. The resulting mixture was evaporated to near dryness, and the residue was dissolved in chloroform. The chloroform solution was washed with water and evaporated, and the residue was heated with a mixture of 200 ml. of methanol and 15 ml. of 5N sodium hydroxide. The mixture then was evaporated to dryness, and the residue was dissolved in a mixture of chloroform and water. The chloroform layer was separated, dried over magnesium sulfate, and evaporated to an oil. A small amount of ethyl acetate was added, and the resulting mixture was scratched. Crystals formed and were collected. The mother liquor filtrate was concentrated and chromatographed to obtain 11.5 grams of crystals which were recrystallized from ethyl ether to give 6.63 grams (50 percent) of the title compound, melting point 97°-98° C.

Workup

  1. customA white suspension resulted
  2. temperatureThe mixture was cooled to b 0° to 10° C.
  3. customgiving rise to a brownish-yellow solution
  4. additionwas poured over a mixture of 200 ml
  5. customThe resulting mixture was evaporated
  6. dissolutionthe residue was dissolved in chloroform
  7. washThe chloroform solution was washed with water
  8. customevaporated
  9. temperaturethe residue was heated with a mixture of 200 ml
  10. customThe mixture then was evaporated to dryness
  11. dissolutionthe residue was dissolved in a mixture of chloroform and water
  12. customThe chloroform layer was separated
  13. dry with materialdried over magnesium sulfate
  14. customevaporated to an oil
  15. additionA small amount of ethyl acetate was added
  16. customCrystals formed
  17. customwere collected
  18. concentrationThe mother liquor filtrate was concentrated
  19. customchromatographed

Sources & evidence

ORD record
ord-ce67e046238847c981c1388f616de564
Source dataset
uspto-grants-1979_01
Patent number
US04133814

Reaction notes

Loading…