Phenethylamine → HCID 178512780, compound

HRID 516192Notes

Reaction equation

HRID 516192 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:10]([OH:14])([OH:13])(=[O:12])=[O:11].CS[C:17](=[NH:19])[NH2:18]>C(O)C>[S:10]([OH:14])([OH:13])(=[O:12])=[O:11].[C:1]1([CH2:7][CH2:8][NH:9][C:17]([NH2:19])=[NH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:7][CH2:8][NH:9][C:17]([NH2:19])=[NH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 178512780HCID 178512780, compoundYield 127%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Phenylethylamine (8.49 g, 70.1 mmol) and S-methylisothiourea sulfate (9.43 g, 33.9 mmol) was dissolved in 100 ml distilled water. Air was passed over the reaction mixture and through 50% NaOH (500 ml) and then through 5% cuprous sulfate (250 ml). The reaction mixture was heated at reflux for 5 hours. Evaporation of the solvent yielded a white powder. The product was isolated by crystallisation from 96% ethanol, washed with cold acetone and diethyl ether and dried in a desecrator. After three crystallizations, the product contained only minor amounts of starting material. The reaction yielded 61.5% (9.14 g) 2-phenylethylguanidine hemisulfate.

Workup

  1. distillationdistilled water
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 5 hours
  4. customEvaporation of the solvent
  5. customyielded a white powder
  6. washwashed with cold acetone and diethyl ether
  7. customdried in a desecrator
  8. customAfter three crystallizations

Sources & evidence

ORD record
ord-fcbd79489cef485a9d5cc6df158b52ce
Source dataset
uspto-grants-2015_08
Patent number
US09109048B2

Reaction notes

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