Ammonia → N-(2-phenoxypropyl)phenylacetamidine p-toluenesulphonate

HRID 1288227Notes

Reaction equation

HRID 1288227 reaction equation
[O:1]([CH:8]([CH3:11])[CH2:9][NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[C:23]1([CH2:29][C:30](N)=[NH:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N>C(O)C.CCOCC>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[O:1]([CH:8]([CH3:11])[CH2:9][NH:10][C:30](=[NH:31])[CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 37183552-Phenoxy-1-propanamineHCID 21504266Phenylacetamidine p-toluenesulphonate

Product 1

HCID 178457535N-(2-phenoxypropyl)phenylacetamidine p-toluenesulphonate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Phenoxypropylamine (6.0 g.) was added to a suspension of phenylacetamidine p-toluenesulphonate (12.4 g.) in absolute ethanol (20 ml.). The mixture was heated to reflux for 4 hours by which time the initially vigorous evolution of ammonia had practically ceased. The resulting solution was cooled somewhat and diluted with ether to give an oil which rapidly crystallised on scratching. The solid was filtered and recrystallised from a mixture of ethanol and water to give N-(2-phenoxypropyl)phenylacetamidine p-toluenesulphonate, m.p. 127°-129°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe resulting solution was cooled somewhat
  3. customto give an oil which
  4. customrapidly crystallised
  5. filtrationThe solid was filtered
  6. customrecrystallised from a mixture of ethanol and water

Sources & evidence

ORD record
ord-719982c498de4dda8dc06af693ee3417
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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