Benzene → HCID 14994410, compound

HRID 893846Notes

Reaction equation

HRID 893846 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.C1C=CC=CC=1.[CH2:16]=[N:17][CH:18]([CH3:20])[CH3:19].[OH-].[Na+]>C(O)(=O)C.O>[S:1]1[CH:5]=[C:4]([CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 4

HCID 241BenzeneHCID 7221Benzo(B)ThiopheneHCID 14798Sodium HydroxideHCID 12108316HCID 12108316, compound

Product 1

HCID 14994410HCID 14994410, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 150 ml of glacial acetic acid was dissolved 33.6 g of benzo[b]thiophene, and 50 ml of a benzene solution of 19.6 g of methylideneisopropylamine was added dropwise to the solution under ice-cooling. After allowing the temperature to rise to room temperature and stirring the mixture for 2 days, the reaction mixture was poured in 500 ml of water and washed thrice with 100 ml of ether. The aqueous layer thus formed was adjusted to pH 10.0 with an aqueous 5N sodium hydroxide solution and extracted 4 times with 100 ml ethyl acetate. The ethyl acetate layer was collected, washed with an aqueous saturated sodium chloride solution, dried by sodium sulfate, dried, then dried under reduced pressure, and the product was subjected to silica gel column chromatography to provide 30.8 g (yield of 60%) of (benzo[b]thiophen-3-ylmethyl)isopropylamine.

Workup

  1. additionwas added dropwise to the solution under ice-
  2. temperaturecooling
  3. customto rise to room temperature
  4. washwashed thrice with 100 ml of ether
  5. customThe aqueous layer thus formed
  6. extractionextracted 4 times with 100 ml ethyl acetate
  7. customThe ethyl acetate layer was collected
  8. washwashed with an aqueous saturated sodium chloride solution
  9. dry with materialdried by sodium sulfate
  10. customdried
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-938cb1750b3c4de2b75fa8e2dbf957a3
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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