Methyl p-toluenesulfonate → HCID 18960688, compound

HRID 1165290Notes

Reaction equation

HRID 1165290 reaction equation
[NH2:1][N:2]1[CH2:6][CH2:5][NH:4][C:3]1=[S:7].[C:8]1([CH3:19])[CH:13]=[CH:12][C:11]([S:14]([O:17]C)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(O)C>[C:8]1([CH3:19])[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:12][CH:13]=1.[NH2:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[S:7][CH3:8]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 125121511-Aminoimidazolidine-2-thione

Product 1

HCID 18960688HCID 18960688, compoundYield 138.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Aminoimidazolidine-2-thione (2.34 g) and methyl p-toluenesulfonate (4.1 g) in ethanol (15 ml) are heated to reflux for 10 minutes, then kept at room temperature for 16 hours. The crystalline precipitate is filtered out and washed with isopropanol to give 4.613 g of 1-amino-2-methylthio-2-imidazoline p-toluenesulfonate as colorless needles, of which 3.79 g is placed in methanol (15 ml) and treated with concentrated aqueous ammonia. After stirring for 6 hours, the mixture is diluted with 20 ml isopropanol. After another 12 hours, 5 ml of liquid is distilled off at atmospheric pressure, and 10 ml isopropanol is added to the remainder. The crystals which separate on cooling are filtered out and washed with isopropanol to give 2.323 g of 1,2-diamino-2-imidazoline p-toluenesulfonate, melting point 190°-190.5° C.

Workup

  1. temperatureto reflux for 10 minutes
  2. filtrationThe crystalline precipitate is filtered out
  3. washwashed with isopropanol

Sources & evidence

ORD record
ord-c4689258ca3c4b9d899d0da9f5050cac
Source dataset
uspto-grants-1990_03
Patent number
US04908446

Reaction notes

Loading…