Sulfuric Acid → HCID 19699091, compound

HRID 1733942Notes

Reaction equation

HRID 1733942 reaction equation
[O:1]=[C:2]1[C:7]2[C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][O:10][C:6]=2[CH2:5][CH2:4][CH2:3]1.[N-:15]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.[NH4+].[OH-]>C(Cl)(Cl)Cl.O>[O:1]=[C:2]1[NH:15][C:7]2[C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][O:10][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 11499367Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-3-carboxylate

Product 1

HCID 19699091HCID 19699091, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 1.0 g of methyl 4,5,6,7-tetrahydro-4-oxo-3-benzofurancarboxylate and 502 mg of sodium azide in 5 ml of chloroform is added dropwise at 32°-36° C. under argon 1.4 ml of sulfuric acid. The reaction mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with 14 ml of water and rendered alkaline with NH4OH and extracted with chloroform. The separated organic layer is washed with water, brine and dried with Na2SO4 and concentrated in vacuo to give 1.0 g of the desired product as a white solid.

Workup

  1. extractionextracted with chloroform
  2. washThe separated organic layer is washed with water, brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6de3b59510064afc803f5d8e62d1fa72
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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