p-Toluidine → 4-ethoxy-N-(4-methylphenyl)benzenesulfonamide

HRID 971308Notes

Reaction equation

HRID 971308 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH2:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH3:19]>C(Cl)Cl>[CH2:18]([O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)(=[O:29])=[O:28])=[CH:25][CH:26]=1)[CH3:19]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 81531DiisopropylethylamineHCID 36883344-Ethoxybenzene-1-sulfonyl chloride

Product 1

HCID 9250104-ethoxy-N-(4-methylphenyl)benzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-4-methylbenzene (1.821 g, 17.0 mmol) was dissolved in DCM (25 mL). N,N-Diisopropylethylamine (3.1 mL, 18.1 mmol) and 4-ethoxy-benzenesulfonyl chloride (2.50 g, 11.3 mmol) were added successively. The reaction mixture was stirred at room temperature overnight and then washed with 10% HCl (2×20 mL) and brine (1×20 mL). Organic phase was dried with sodium sulfate before filtering and removal of solvent. The desired product, e.g. 4-ethoxy-N-(4-methylphenyl)benzenesulfonamide (3.087 g, 94%), was obtained as a colorless solid, in 99.2% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. washwashed with 10% HCl (2×20 mL) and brine (1×20 mL)
  2. dry with materialOrganic phase was dried with sodium sulfate
  3. filtrationbefore filtering
  4. customremoval of solvent

Sources & evidence

ORD record
ord-3f9de7de5b424a2083262a8f87fa9f54
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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