Acetophenone → HCID 87119832, compound

HRID 2366347Notes

Reaction equation

HRID 2366347 reaction equation
[OH-].[Na+].[NH:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[NH2:4].[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[CH3:16]>O>[C:18]1(/[C:15](=[N:4]/[NH:3][C:5]2[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:12])=[O:13])=[CH:7][CH:6]=2)/[CH3:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 668254-Hydrazinobenzenesulfonic acid

Product 1

HCID 87119832HCID 87119832, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Sodium hydroxide (400 mg, 10 mmol) in 10 mL of water was added to a solution of 4-hydrazino-benzenesulfonic acid (1.88 g, 10 mmol) in 20 mL of water. Acetophenone (1.32 g, 11 mmol) was then added, and the mixture was heated to 100° C. overnight. The resulting mixture was then cooled and washed with ether. The pH of the aqueous solution was then adjusted to 4 with conc. HCl. Water was removed under vacuum, and methanol was added. The solution was filtered and concentrated to give product (680 mg) as a yellow solid (MS: (M+H)+=291.15).

Workup

  1. temperatureThe resulting mixture was then cooled
  2. washwashed with ether
  3. customWater was removed under vacuum, and methanol
  4. additionwas added
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6be890565233499681089df37448432d
Source dataset
uspto-grants-2014_04
Patent number
US08697739B2

Reaction notes

Loading…