2-Phenylacetophenone → 4-(2-Oxo-2-phenylethyl)benzene-1-sulfonamide

HRID 343074Notes

Reaction equation

HRID 343074 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[C:6]1([C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH4+:21].[OH-]>CC(C)=O>[NH2:21][S:2]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:13])=[CH:20][CH:19]=1)(=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 99482-PhenylacetophenoneHCID 14923Ammonium HydroxideHCID 24638Chlorosulfonic acid

Product 1

HCID 222857924-(2-Oxo-2-phenylethyl)benzene-1-sulfonamideYield 29%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Chlorosulfonic acid (1781 g, 1018 mL, 15.29 mol) was treated portionwise with deoxybenzoin (400 g, 2.04 mol) at such a rate that the internal temperature was maintained between 5° and 15° C. The mixture was warmed to room temperature and maintained at that temperature for an additional 14 hours. The mixture was poured cautiously into ice water. The crude sulfonyl chloride was filtered and added portionwise to a solution of acetone (600 mL) and concentrated NH4OH (551 mL, 8.15 mol), yielding a pale yellow suspension. The crude precipitate was collected by vacuum filtration, and triturated with boiling acetone (1.5 L). Filtration afforded 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one (162 g, 29%) as an off-white powder: 1H NMR (DMSO-d6, 300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 2H), 7.44 (d, J=8.26, 2H), 7.30 (br s, 2H), 4.52 (s, 2H).

Workup

  1. temperaturewas maintained between 5° and 15° C
  2. temperaturemaintained at that temperature for an additional 14 hours
  3. filtrationThe crude sulfonyl chloride was filtered
  4. customyielding a pale yellow suspension
  5. filtrationThe crude precipitate was collected by vacuum filtration
  6. customtriturated with boiling acetone (1.5 L)
  7. filtrationFiltration

Sources & evidence

ORD record
ord-4b84169acae64933a2ca783eddbe44b2
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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