Ammonia → 2,1,3-benzoxadiazole-4-sulfonamide

HRID 1722194Notes

Reaction equation

HRID 1722194 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[C:9]([S:10](Cl)(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12.O1CCCC1.[NH3:19].[OH-].[NH4+]>O>[N:1]1[O:2][N:3]=[C:4]2[C:9]([S:10]([NH2:19])(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 27354462,1,3-Benzoxadiazole-4-sulfonyl chloride

Product 1

HCID 27565902,1,3-benzoxadiazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3.0 g of 2,1,3-benzoxadiazole-4-sulfonyl chloride and 200 mL of tetrahydrofuran at -30° C. was added 10 mL of ammonia under an inert atmosphere. The resulting suspension was stirred at ambient temperature for 3 hours. Concentrated ammonium hydroxide (20 mL) and water (20 mL) were added. The reaction was extracted with ethyl acetate and the organic extracts were combined, dried over magnesium sulfate, filtered, and stripped to give a crude solid. Recrystallization from chlorobutaneethanol afforded 1.82 g of the title compound as an orange-tan solid, m.p. 157°-159° C.

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customto give a crude solid
  5. customRecrystallization from chlorobutaneethanol

Sources & evidence

ORD record
ord-d526aa1512634915bc4d4f2fc5c0b075
Source dataset
uspto-grants-1989_08
Patent number
US04854962

Reaction notes

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