Phenethylamine → 4-((2-Phenylethyl)aminocarbonyl)benzenesulfonamide

HRID 22415

Reaction equation

HRID 22415 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([OH:3])=O.C(N(CC)CC)C.ClC(OCC)=O.[C:27]1([CH2:33][CH2:34][NH2:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[C:27]1([CH2:33][CH2:34][NH:35][C:1]([C:4]2[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=2)=[O:3])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 8739CarzenideHCID 10928Ethyl chloroformate

Product 1

HCID 199707484-((2-Phenylethyl)aminocarbonyl)benzenesulfonamideYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

20.1 g (0.1 mol) of 4-carboxy-benzenesulfonamide were suspended in 300 ml of anhydrous tetrahydrofuran, and 15.2 ml (0.11 mol) of triethylamine were added dropwise at 0° C., while stirring. After 30 minutes, 10.5 ml (0.11 mol) of ethyl chloroformate were added dropwise at 0° C., the mixture was stirred at this temperature for 1 hour and cooled to -10° C., and 12.1 g (0.1 mol, 12.5 ml) of 2-phenylethylamine in 30 ml of anhydrous tetrahydrofuran were added dropwise. After 1 hour at 0° C., the mixture was warmed to 20° C. and concentrated in vacuo and the solid residue was treated with water, filtered off with suction and recrystallized from ethanol to give 20.4 g of product, melting point 243° to 245° C.

Workup

  1. stirringthe mixture was stirred at this temperature for 1 hour
  2. waitAfter 1 hour at 0° C.
  3. temperaturethe mixture was warmed to 20° C.
  4. concentrationconcentrated in vacuo
  5. additionthe solid residue was treated with water
  6. filtrationfiltered off with suction
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-350c9a4b7662438bb680d09920db4e0a
Source dataset
uspto-grants-1995_06
Patent number
US05428046

Linked notes

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