Dextroamphetamine → 4-Methyl-N-(1-methyl-2-phenylethyl)benzenesulfonamide

HRID 224565

Reaction equation

HRID 224565 reaction equation
[CH3:1][C@H:2]([NH2:10])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C1C=CC=CC=1>[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([NH:10][CH:2]([CH3:1])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 5826DextroamphetamineHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 132498614-Methyl-N-(1-methyl-2-phenylethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Dextro amphetamine (200 g) and triethylamine (164 g) were dissolved in 1500 ml. of benzene. A solution of p-toluene sulfonyl chloride (310g) in 500 ml. of benzene was added dropwise to the cooled solution during one hour. The reaction mixture was stirred for three hours at room temperature, then allowed to stand for approximately 16 hours (over night) at room temperature (approximately 20° C.). The salts were filtered off and the benzene solution was washed with dilute HCl, water and brine. Evaporation of the solvent afforded an oil.

Workup

  1. waitto stand for approximately 16 hours
  2. customat room temperature
  3. custom(approximately 20° C.)
  4. filtrationThe salts were filtered off
  5. washthe benzene solution was washed with dilute HCl, water and brine
  6. customEvaporation of the solvent
  7. customafforded an oil

Sources & evidence

ORD record
ord-b403412b2678470f8919b8be94d0df2d
Source dataset
uspto-grants-1980_11
Patent number
US04233217

Linked notes

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