Benzene → HCID 19898819, compound

HRID 1196500Notes

Reaction equation

HRID 1196500 reaction equation
[N:1]1([C:6](=[O:24])[CH2:7][C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[N:13][C:12]=23)[CH:5]=[CH:4]N=[CH:2]1.[CH2:25](NCCC)[CH2:26]C.[CH:32]1C=CC=CC=1>>[CH3:23][C:20]1[CH:19]=[CH:18][C:17]([C:9]2[C:8]([CH2:7][C:6]([N:1]([CH2:2][CH2:25][CH3:26])[CH2:5][CH2:4][CH3:32])=[O:24])=[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 8902DipropylamineHCID 19898814HCID 19898814, compound

Product 1

HCID 19898819HCID 19898819, compoundYield 39.6%

Procedure

A mixture of 3.25 g (0.010 mole) of 3-[2-(1H-imidazole-1-yl)-2-oxoethyl]-2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine (prepared from 2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-acetic acid and 1,1'-carbonyldiimidazole) and 1.1 g (0.011 mole) of dipropylamine in 25 ml of benzene was stirred at reflux for 5 hours. After cooling, the reaction mixture was washed with water, dried over magnesium sulfate, and concentrated in vacuo (2.6 g). The crude solid residue was purified by a liquid-solid extraction with isopropyl ether in a soxhlet. The purified product was collected by filtration from the isopropyl ether (extraction solvent) to yield 1.4 g (39.6%) of golden yellow crystals, mp 110°-111° C.

Workup

  1. temperatureat reflux for 5 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo (2.6 g)
  6. customThe crude solid residue was purified by a liquid-solid extraction with isopropyl ether in a soxhlet
  7. filtrationThe purified product was collected by filtration from the isopropyl ether (extraction solvent)

Sources & evidence

ORD record
ord-bf5c9a51b94a404fb8fd89e5a5903f8c
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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