Hydrochloric Acid → HCID 18947226, compound

HRID 1769158Notes

Reaction equation

HRID 1769158 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1([CH2:12][OH:13])[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[CH2:6][CH2:5][CH2:4]1.[H-].[Na+].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:22]Cl.Cl>O1CCCC1>[CH3:1][N:2]([CH3:14])[C:3]1([CH2:12][O:13][CH2:22][C:21]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:19]([O:18][CH3:17])[CH:20]=2)[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 15225070HCID 15225070, compound

Product 1

HCID 18947226HCID 18947226, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

15 ml of tetrahydrofuran containing 2.57 g of 4-dimethylamino-4-hydroxymethyl-4,5,6,7-tetrahydro-1-benzothiophen obtained in Example 1 was added to an ice-cooled suspension of 60% sodium hydride (0.54 g) in tetrahydrofuran. 15 ml of tetrahydrofuran containing 2.90 g of 3,4,5-trimethoxybenzyl chloride was further added to the reaction mixture, followed by refluxing under heat for 24 hours. After cooling, the reaction mixture was poured into hydrochloric acid solution, and washed with ether. The aqueous phase was added with a sodium hydroxyde solution for making the system basic, followed by extracting with chloroform. After the chloroform phase was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography to obtain 2.79 g of the title compound as a pale yellow oily product.

Workup

  1. temperaturecooled
  2. temperatureby refluxing
  3. temperatureunder heat for 24 hours
  4. temperatureAfter cooling
  5. washwashed with ether
  6. additionThe aqueous phase was added with a sodium hydroxyde solution
  7. extractionby extracting with chloroform
  8. washAfter the chloroform phase was washed with water
  9. customdried
  10. customthe solvent was removed
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30a03775a13443ef94112e56a045de3f
Source dataset
uspto-grants-1995_01
Patent number
US05380748

Reaction notes

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