Hydrochloric Acid → N-(2-ethyl-4-propionylphenyl)methanesulfonamide

HRID 607533Notes

Reaction equation

HRID 607533 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH3:9].[CH3:10][S:11](Cl)(=[O:13])=[O:12].[Cl-].[Cl-].[Cl-].[Al+3].[C:19](Cl)(=[O:22])[CH2:20][CH3:21].Cl>N1C=CC=CC=1.ClCCl.C1(C)C=CC=CC=1>[CH2:8]([C:3]1[CH:4]=[C:5]([C:19](=[O:22])[CH2:20][CH3:21])[CH:6]=[CH:7][C:2]=1[NH:1][S:11]([CH3:10])(=[O:13])=[O:12])[CH3:9]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 113572-EthylanilineHCID 31297Methanesulfonyl chlorideHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67047217N-(2-ethyl-4-propionylphenyl)methanesulfonamideYield 43%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-1-ethylbenzene (5 ml, 5.0 g, 41 mmol) in pyridine (3.5 ml) and dichloromethane (10 ml), methanesulfonyl chloride (3.2 ml. 4.7 g, 41 mmol) was added dropwise over 10 min at 0° C. The reaction mixture was stirred at rt for 1 hour. After cooling to 0° C. aluminum trichloride (13.8 g, 103 mmol) was added to the reaction mixture carefully. Then propionyl chloride (3.6 ml, 3.8 g, 41 mmol) was added dropwise over 15 min. The reaction mixture was diluted with toluene (25 ml) and poured into 2 M hydrogen chloride aqueous solution (50 ml) under stirring at 0° C. The precipitate solids were filtered, washed with water and dried in vacuo to get a desired product (4.5 g, 43% yield) as yellow solids.

Workup

  1. additionwas added to the reaction mixture carefully
  2. stirringunder stirring at 0° C
  3. filtrationThe precipitate solids were filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b1f50ce01698409bab394c18e0dba797
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

Loading…