Ammonium Hydroxide → HCID 14254936, compound

HRID 2352464Notes

Reaction equation

HRID 2352464 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10](Cl)(=[O:12])=[O:11].[OH-].[NH4+:15]>CC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10]([NH2:15])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 15051878HCID 15051878, compound

Product 1

HCID 14254936HCID 14254936, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Six grams of crude 3-(2-methoxyethyl)thiophene-2-sulfonyl chloride was dissolved in 25 mL of acetone and added dropwise with stirring at ambient temperature to 25 mL of concentrated aqueous ammonium hydroxide. The reaction mixture was allowed to stand overnight and the acetone removed by evaporation. The aqueous residue was extracted with three 100 mL portions of methylene chloride which were combined, dried over magnesium sulfate, filtered and evaporated to yield a residue which was a mixture of an oil and a solid. The sulfonamide was isolated by passing the residue through a 30 cm high by 80mm diameter column of silica gel using 1:1 ethyl acetate mixed hexanes solvent system and taking 100 mL fractions. The desired product came off in fractions 4 to 12. After evaporation of the solvent 1.84 grams was obtained, m.p. 64°-73° C. Analysis by mass spectroscopy showed a molecular weight of 221 AMU in agreement for the desired sulfonamide.

Workup

  1. additionadded dropwise
  2. customthe acetone removed by evaporation
  3. extractionThe aqueous residue was extracted with three 100 mL portions of methylene chloride which
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a residue which
  8. additiona mixture of an oil

Sources & evidence

ORD record
ord-5185e12624d5457a83cb7925933c5abd
Source dataset
uspto-grants-1989_10
Patent number
US04877440

Reaction notes

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