Ammonia → 6-Bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

HRID 746287Notes

Reaction equation

HRID 746287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:15](Cl)(=[O:17])=[O:16])[C:5]2[O:10][S:9](=[O:12])(=[O:11])[C:8]([CH3:13])=[CH:7][C:6]=2[CH:14]=1.[NH3:19]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:15]([NH2:19])(=[O:17])=[O:16])[C:5]2[O:10][S:9](=[O:12])(=[O:11])[C:8]([CH3:13])=[CH:7][C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 135920726-Bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl chloride

Product 1

HCID 135920736-Bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 180 g of 6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl chloride in 500 ml of tetrahydrofuran is added dropwise over 30 minutes to 307 ml of a 30% aqueous solution of ammonia. The mixture is stirred for 30 minutes at 20° C. and concentrated under reduced pressure at 45° C. The residue is triturated with 200 ml of ether. The precipitate is isolated, washed with water and dried at 45° C., affording 63.2 g of 6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of m.p. 243°-245° C. (crystallisation from ethanol).

Workup

  1. concentrationconcentrated under reduced pressure at 45° C
  2. customThe residue is triturated with 200 ml of ether
  3. customThe precipitate is isolated
  4. washwashed with water
  5. customdried at 45° C.
  6. customaffording
  7. custom63.2 g of 6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of m.p. 243°-245° C. (crystallisation from ethanol)

Sources & evidence

ORD record
ord-f0f97717328344668e13d3f03a1a173f
Source dataset
uspto-grants-1986_07
Patent number
US04603211

Reaction notes

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