Sodium Hydroxide → 1,3-dimethyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole

HRID 1769086Notes

Reaction equation

HRID 1769086 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH3:15][C:16]1[S:17][C:18]([CH3:34])=[C:19]2[CH2:23][N:22](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:21][C:20]=12.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:15][C:16]1[S:17][C:18]([CH3:34])=[C:19]2[CH2:23][NH:22][CH2:21][C:20]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189470571,3-Dimethyl-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrroleHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 189470401,3-dimethyl-5,6-dihydro-4H-thieno[3,4-c]pyrroleYield 67.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A mixture of 38 ml of a 3.4M solution of sodium bis(2-methoxyethoxy)aluminium hydride in toluene and 10 ml of dry toluene is added, at room temperature, to a suspension of 9.1 g (0.03 mol) of 1,3-dimethyl-5-tosyl-5,6-dihydro-4H-thieno [3,4-c]pyrrole in 42 ml of dry toluene. The mixture is then heated at reflux for 2 h 30 min, cooled to room temperature, and poured into 400 ml of 1N sodium hydroxide. The organic phase is washed with 3 times 50 ml of water and extracted with a 0.5N hydrochloric acid solution. The solid, precipitated by addition of a sodium carbonate solution, is filtered off, washed with water and dried. 3.12 g of product are obtained. Melting point: 110°-112° C. (with decomposition).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 2 h 30 min
  3. washThe organic phase is washed with 3 times 50 ml of water
  4. extractionextracted with a 0.5N hydrochloric acid solution
  5. customThe solid, precipitated by addition of a sodium carbonate solution
  6. filtrationis filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6804808e825b42148b0281104f3d6160
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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