Isopropylamine → HCID 178457611, compound

HRID 2212107Notes

Reaction equation

HRID 2212107 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].CS[C:8](=[NH:10])[NH2:9].[CH:11]([NH2:14])([CH3:13])[CH3:12]>O>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH:11]([NH:14][C:8]([NH2:10])=[NH:9])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 178457611HCID 178457611, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of S-methylisothiourea sulfate (65.9 g, 250 mmol) in water (100 ml) was cooled with an ice/salt bath. To the solution was added isopropylamine (42.5 ml, 500 mmol) dropwise with stirring. The reaction mixture was allowed to stir at room temperature for 16 hours after the addition of amine was completed and was then refluxed for about 4 to about 5 hours. The solution was evaporated to dryness under the reduced pressure and the residue was crystallized from 95% EtOH, to give isopropylguanidine sulfate as colorless needles (16.12 g, 81.01 mmol, 32%). 1H NMR (300 MHz, D2O): δ 3.72 (m, 1H), 1.27 (d, J=6.4 Hz, 6H); 13C NMR: δ 158.45, 46.50, 24.11; IR: 1675, 1623, 1071 cm−1.

Workup

  1. stirringto stir at room temperature for 16 hours
  2. temperaturewas then refluxed for about 4 to about 5 hours
  3. customThe solution was evaporated to dryness under the reduced pressure
  4. customthe residue was crystallized from 95% EtOH

Sources & evidence

ORD record
ord-0e54454f2c3343dd9b5864a19d325cb0
Source dataset
uspto-grants-2006_09
Patent number
US07101902B2

Reaction notes

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