N-Acetylimidazolidinone → 1-Acetyl-2(3-isopropyl-1-methyl-5-pyrazolyl)amino-2-imidazoline

HRID 903036Notes

Reaction equation

HRID 903036 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1.[C:11]([N:14]1[CH2:18][CH2:17][NH:16][C:15]1=O)(=[O:13])[CH3:12]>P(Cl)(Cl)(Cl)=O>[C:11]([N:14]1[CH2:18][CH2:17][N:16]=[C:15]1[NH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 79350N-AcetylimidazolidinoneHCID 27594993-Isopropyl-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 127637871-Acetyl-2(3-isopropyl-1-methyl-5-pyrazolyl)amino-2-imidazoline

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

5-amino-3-isopropyl-1-methyl pyrazole (described in British Patent 1,057,740) (19.3 g) was dissolved in 180 ml phosphorus oxychloride (POCl3). 1-Acetyl-2-imidazolidinone (J. Chem Soc 1964, 178) (20.1 g) was added. This reaction mixture was stirred at 55° for 40 hr. The solvents were concentrated in vacuum, ice and methylene chloride were added and the mixture neutralized with 25% sodium hydroxide in water. The methylene chloride layer was dried over MgSO4 and then concentrated and the residue crystallized from isopropyl alcohol and ether to give 12.73 g. of product, mp 145°-147° C.

Workup

  1. concentrationThe solvents were concentrated in vacuum, ice and methylene chloride
  2. additionwere added
  3. dry with materialThe methylene chloride layer was dried over MgSO4
  4. concentrationconcentrated
  5. customthe residue crystallized from isopropyl alcohol and ether
  6. customto give 12.73 g

Sources & evidence

ORD record
ord-be18c7669df64f19b3683728f027f9ef
Source dataset
uspto-grants-1980_10
Patent number
US04226773

Reaction notes

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