Iodoethane → N-(3-acetylphenyl)-N-ethyl-4-methylbenzenesulfonamide

HRID 1247965Notes

Reaction equation

HRID 1247965 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].C[O-].[Na+].[CH2:24](I)[CH3:25]>CN(C)C=O>[C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:24][CH3:25])[S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 220585N-(3-Acetylphenyl)-4-methylbenzenesulfonamideHCID 10942334Sodium Methoxide

Product 1

HCID 20280466N-(3-acetylphenyl)-N-ethyl-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 29 g portion of N-(3-acetylphenyl)-4-methylbenzenesulfonamide was dissolved in 250 ml of dimethylformamide with stirring. This mixture was treated with 6.5 g of sodium methoxide and stirred for 30 minutes, then 20 g of ethyl iodide was added. This mixture was stirred at room temperature for one hour, then at reflux for 5 hours. The dimethylformamide was removed in vacuo, the residue shaken with 150 ml of water, the mixture adjusted to pH 4 with 10N sodium hydroxide and then cooled to 0° C. The precipitate was collected, washed twice with water and then air dried, giving 31.5 g of N-(3-acetylphenyl)-N-ethyl-4-methylbenzenesulfonamide.

Workup

  1. stirringstirred for 30 minutes
  2. stirringThis mixture was stirred at room temperature for one hour
  3. temperatureat reflux for 5 hours
  4. customThe dimethylformamide was removed in vacuo
  5. stirringthe residue shaken with 150 ml of water
  6. customThe precipitate was collected
  7. washwashed twice with water
  8. customair dried

Sources & evidence

ORD record
ord-79a78215d79d4734b818b9fb08dcdda8
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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