Sodium Azide → HCID 14390577, compound

HRID 2232369Notes

Reaction equation

HRID 2232369 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]2[CH:11]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:9][C:8]=2[CH:16]=1)(=O)C.[N-:17]=[N+]=[N-].[Na+].[CH3:21][C:22]([O-:24])=O.[Na+]>C(O)(=O)C.OS(O)(=O)=O>[C:22]([NH:17][C:4]1[CH:5]=[CH:6][C:7]2[CH:11]=[C:10]([S:12](=[O:13])(=[O:14])[NH2:15])[S:9][C:8]=2[CH:16]=1)(=[O:24])[CH3:21]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 13922881HCID 13922881, compound

Product 1

HCID 14390577HCID 14390577, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 6-acetylbenzo[b]thiophene-2-sulfonamide (5.1 g, 0.02 mole) in glacial acetic acid (50 ml) and concentrated H2SO4 (20 ml) was stirred and heated to 65° C. Sodium azide (5.0 g, 0.077 mole) was added in portions over a 1 hour period. After heating the mixture at 80° C. for another 3 hours, it was poured into a stirred, saturated NaOAc solution (500 ml) cooled in an ice bath. The resulting mixture was refrigerated overnight. The solid was collected, resuspended in water (300 ml), and recollected to obtain 5.25 g (97%) of crude product, m.p. 214°-217° C. Recrystallizations from CH3OH with charcoal decolorization and from CH3CN afforded 1.5 g of 6-acetamido-2-sulfamoylbenzo[b]thiophene, m.p. 231°-232.5° C.

Workup

  1. temperatureAfter heating the mixture at 80° C. for another 3 hours
  2. temperaturecooled in an ice bath
  3. customThe solid was collected
  4. customto obtain 5.25 g (97%) of crude product, m.p. 214°-217° C
  5. customRecrystallizations from CH3OH with charcoal decolorization

Sources & evidence

ORD record
ord-c019d1725ef94fb88c1b21847cd91df0
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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