Sodium methanethiolate → 5-Methyl-2-methylthiomethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900747Notes

Reaction equation

HRID 1900747 reaction equation
Br[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[CH3:18][S-:19].[Na+]>CN(C)C=O>[CH3:15][C:13]1[CH:14]=[C:5]2[CH2:4][CH:3]([CH2:2][S:19][CH3:18])[O:17][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:16])[CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 233696165-Methyl-2-methylthiomethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.942 g) in dimethylformamide (120 ml) was combined with aqueous 15% sodium thiomethoxide (9.4 ml), and stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. Water was added to the residue, and extracted with chloroform. The chloroform extract was washed with diluted hydrochloric acid, diluted caustic soda and water in this order, and dried. The resultant material was crystallized from tetrahydrofuran to obtain 2.355 g of the title compound as colorless prisms (mp. 203°-206° C.) (yield: 90.1%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. washwas washed with diluted hydrochloric acid, diluted caustic soda and water in this order
  6. customdried
  7. customThe resultant material was crystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-3e6ee8ad335249e59a9db4a53bacc624
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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