Water → HCID 178512780, compound

HRID 2116444Notes

Reaction equation

HRID 2116444 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].O.[OH-].[Na+]>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

6

Reactant 4

HCID 962WaterHCID 1001PhenethylamineHCID 14798Sodium HydroxideHCID 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 destilled 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 desicator. After three crystallisations, the product contained only minor amounts of starting material. The reaction yielded 61.5% (9.14 g) 2-phenylethylguanidine hemisulfate.

Workup

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

Sources & evidence

ORD record
ord-9010796a1a5e4279a571a41cb9cba6b8
Source dataset
uspto-grants-2008_10
Patent number
US07439228B2

Reaction notes

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