Ammonia → HCID 22490755, compound

HRID 1415785Notes

Reaction equation

HRID 1415785 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7](=O)[CH2:8][CH:9]([CH2:12][CH3:13])[CH:10]=O)=[CH:5][CH:4]=1.[S:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)(=[O:20])(=[O:19])[NH2:18].N>C(O)(=O)C>[CH2:12]([C:9]1[CH:8]=[C:7]([C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:25]([C:24]2[CH:26]=[CH:27][C:21]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:22][CH:23]=2)[CH:10]=1)[CH3:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5333SulfanilamideHCID 21862774HCID 21862774, compound

Product 1

HCID 22490755HCID 22490755, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.47 g (2.1 mmol) of 2-(4-methoxyphenacyl)butyraldehyde [prepared as described in step (ii) above] and 0.44 g (2.5 mmol) of 4-sulfamoylaniline were dissolved in 5 ml of acetic acid, and the resulting solution was heated under reflux for 2 hours. At the end of this time, the mixture was cooled to room temperature, concentrated aqueous ammonia was added to adjust its pH to a value of 8.0 and the mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue was applied to a silica gel chromatography column, eluted with a 3:2 by volume mixture of hexane and ethyl acetate, to give 0.57 g (yield 76%) of the title compound as a pale yellow powder, melting at 154-156° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. washeluted with a 3:2 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-cdffb44c80994adfb6a3401797f8348b
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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