Phenacyl bromide → HCID 19101522, compound

HRID 1974435Notes

Reaction equation

HRID 1974435 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(N(CC)CC)C.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23]>CO.C(O)C>[CH3:1][S:2]([NH:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 37325774-(Methylsulfonamido)aniline

Product 1

HCID 19101522HCID 19101522, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
5 °C

Procedure

4-Methanesulfonamidoaniline (150 g, 0.8 mol) and triethylamine (81.4 g, 0.8 mol) were combined with 2.4 liters of 1:1 methanol/ethanol in a five liter round bottom flask, and stirred mechanically until all solids dissolved. 2-Bromoacetophenone (240 g, 1.2 mol) was added as a solid in several portions over a twenty minute period. The reaction was stirred at 25° C. for 14 h, during which an off-white precipitate formed. The mixture was chilled to 5° C., then the product was collected by filtration, washed with cold ethanol and dried under vacuum to yield 152 g (62%) of 2-(4-methanesulfonamidoanilino)acetophenone as an off-white solid, m.p. 165°-167° C. NMR and mass spectral data were consistent with the assigned structure.

Workup

  1. dissolutiondissolved
  2. stirringThe reaction was stirred at 25° C. for 14 h, during which an off-white precipitate
  3. customformed
  4. filtrationthe product was collected by filtration
  5. washwashed with cold ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-775d80f75ceb4c99b38e8d3af55eddb9
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

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