Triethylamine → HCID 14538888, compound

HRID 1762427Notes

Reaction equation

HRID 1762427 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C(N(CC)CC)C>C(O)C>[N:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 178418431pyridine-4-thiol

Product 1

HCID 14538888HCID 14538888, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 ml of ethanol were suspended 6.66 g of 4-mercaptopyridine and 16.9 g of N-(4-bromobutyl)phthalimide. To the suspension was added 9.09 g of triethylamine, and the mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure. To the residue was added 300 ml of water, and the mixture was subjected to extraction twice with dichloromethane. The extract solutions were combined, washed with an aqueous saline solution, then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel (500 g) column chromatography, using as the developer a mixture of hexane and ethyl acetate (1:2), followed by elution with ethyl acetate. The eluate was concentrated under reduced pressure. To the concentrate were added ethyl acetate and hexane. Resulting powders were collected by filtration to give N-[4-(4-pyridylthio)butyl]phthalimide as a colorless powdery product, m.p. 106.5°-107.5° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionTo the residue was added 300 ml of water
  3. extractionthe mixture was subjected to extraction twice with dichloromethane
  4. washwashed with an aqueous saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. additiona mixture of hexane and ethyl acetate (1:2)
  8. washfollowed by elution with ethyl acetate
  9. concentrationThe eluate was concentrated under reduced pressure
  10. additionTo the concentrate were added ethyl acetate and hexane
  11. customResulting powders
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-990e45f5f2b74ce0b9fc70e41c659569
Source dataset
uspto-grants-1989_05
Patent number
US04833134

Reaction notes

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