Phosphorus oxychloride → 1-Acetyl-2(3-isopropyl-1-methyl-5-pyrazolyl)amino-2-imidazoline

HRID 224803

Reaction equation

HRID 224803 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:16]([N:19]1[CH2:23][CH2:22][NH:21][C:20]1=O)(=[O:18])[CH3:17]>>[C:16]([N:19]1[CH2:23][CH2:22][N:21]=[C:20]1[NH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 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

Procedure

5-amino-3-isopropyl-1-methyl pyrazole (described in British Pat. No. 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. dissolution1,057,740) (19.3 g) was dissolved in 180 ml
  2. concentrationThe solvents were concentrated in vacuum, ice and methylene chloride
  3. additionwere added
  4. dry with materialThe methylene chloride layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue crystallized from isopropyl alcohol and ether
  7. customto give 12.73 g

Sources & evidence

ORD record
ord-7fc93ac678ee4782b5fb630a19c1546f
Source dataset
uspto-grants-1980_11
Patent number
US04234594

Linked notes

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