Sodium Carbonate → 2-(4-Amino-1,3-dimethyl-5-pyrazolyl)-4,5-dimethylimidazoline

HRID 2417662Notes

Reaction equation

HRID 2417662 reaction equation
[NH2:1][C:2]1[C:3]([CH3:10])=[N:4][N:5]([CH3:9])[C:6]=1[C:7]#[N:8].[NH2:11][CH:12]([CH:14](N)[CH3:15])[CH3:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:3]([CH3:10])=[N:4][N:5]([CH3:9])[C:6]=1[C:7]1[NH:11][CH:12]([CH3:13])[CH:14]([CH3:15])[N:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 1363622,3-ButanediamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 123358164-Amino-1,3-dimethyl-1H-pyrazole-5-carbonitrile

Product 1

HCID 140065832-(4-Amino-1,3-dimethyl-5-pyrazolyl)-4,5-dimethylimidazolineYield 91.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7 g (0.05 mol) of 4-amino-5-cyano-1,3-dimethylpyrazole, 5 g (0.057 mol) of 2,3-diaminobutane and 10.5 g (0.055 mol) of p-toluene sulfonic acid hydrate is heated in an oil bath at 180°-200° C. for seven hours. The yellow melt is dissolved in 200 ml of chloroform and stirred with 100 ml of 20% aqueous sodium carbonate solution. The organic layer is separated, dried over MgSO4 and evaporated in vacuo to give 9.5 g of 2-(4-amino-1,3-dimethyl-5-pyrazolyl)-4,5-dimethylimidazoline and characterized as a dihydrochloride salt, mp 250° C. from 20% isopropanolic HCl and ethyl acetate.

Workup

  1. temperatureis heated in an oil bath at 180°-200° C. for seven hours
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a6e93a42d1764eadad75bcf770abc096
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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