Ammonium Hydroxide → 2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonamide

HRID 280470Notes

Reaction equation

HRID 280470 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11](Cl)(=[O:13])=[O:12])[C:4]=2[O:3]1.[OH-].[NH4+:17]>O1CCCC1>[CH3:1][C:2]1([CH3:15])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:17])(=[O:13])=[O:12])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 134241792,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonyl chloride

Product 1

HCID 134241802,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 26 g of 2,3-dihydro-2,2-dimethyl-7-benzofuransulfonyl chloride prepared in Example 1, in 130 ml of tetrahydrofuran, was cooled in an ice-water bath while about 30 ml of concentrated aqueous ammonium hydroxide was added portionwise at 10° to 30° C. The resulting suspension was stirred at room temperature for 3 hours, then the solvent was evaporated under reduced pressure. The residue was stirred in 150 ml of water for 0.5 hour, then filtered. The crude, wet solid was dissolved in chloroform and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give a dry solid. The solid was washed once with about 100 ml of hot toluene to give 20 g of 2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide, m.p. 163°-165° C.

Workup

  1. additionwas added portionwise at 10° to 30° C
  2. customthe solvent was evaporated under reduced pressure
  3. stirringThe residue was stirred in 150 ml of water for 0.5 hour
  4. filtrationfiltered
  5. dissolutionThe crude, wet solid was dissolved in chloroform
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customto give a dry solid
  9. washThe solid was washed once with about 100 ml of hot toluene

Sources & evidence

ORD record
ord-6db622ff9db94ee8a79f8d1a19d901cb
Source dataset
uspto-grants-1986_05
Patent number
US04589909

Reaction notes

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