Sodium Azide → Ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo(c]thiophene-1-carboxylate

HRID 1936861Notes

Reaction equation

HRID 1936861 reaction equation
Br[CH:2]1[CH2:17][CH2:16][C:5]2=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:7][C:8]([S:9][CH3:10])=[C:4]2[C:3]1=[O:18].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)C=O.O>[N:19]([CH:2]1[CH2:17][CH2:16][C:5]2=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:7][C:8]([S:9][CH3:10])=[C:4]2[C:3]1=[O:18])=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 15885619Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

Product 1

HCID 18388306Ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo(c]thiophene-1-carboxylateYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (5.24 g) was suspended in N,N-dimethylformamide (80 ml); a solution of sodium azide (1.95 g) in water (12 ml) was added at 0° C. After the reaction mixture was stirred at room temperature for 4 hours, it was poured over water (50 ml) and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:9 to 1:2, v/v) to yield ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (3.77 g, 80.7%), which was then recrystallized from ethyl acetate-hexane. Colorless needles. Melting point 163-164° C. (decomposed).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with ethyl acetate-hexane (1:9 to 1:2

Sources & evidence

ORD record
ord-d7506e488d2144b5af6a50e1ff2b99ea
Source dataset
uspto-grants-2002_05
Patent number
US06391905B1

Reaction notes

Loading…