Water → HCID 14403280, compound

HRID 1649716Notes

Reaction equation

HRID 1649716 reaction equation
[C:1]1(=[O:19])[N:5]([CH2:6][CH2:7][CH2:8][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12.F[C:21]1[CH:33]=[CH:32][C:24]([C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:23][CH:22]=1.[H-].[Na+].O>CS(C)=O>[C:4]1(=[O:14])[N:5]([CH2:6][CH2:7][CH2:8][C:9]2[N:10]=[CH:11][N:12]([C:21]3[CH:33]=[CH:32][C:24]([C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:23][CH:22]=3)[CH:13]=2)[C:1](=[O:19])[C:2]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:3]12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1013593-(4-Fluorobenzoyl)propionic acidHCID 1785149894-(3-Phthalimidopropyl)-imidazole

Product 1

HCID 14403280HCID 14403280, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5.10 g (20 mmol) of 4-(3-phthalimidopropyl)-imidazole followed by 3.92 g (20 mmol) of 3-(4-fluorobenzoyl)-propionic acid are added portionwise to a suspension of 1.20 g (40 mmol) of sodium hydride (80% on paraffin oil) in 50 ml of dimethyl sulphoxide. The reaction mixture is initially stirred at room temperature until gas evolution ceases and then at 100° C. for 17 hours. After cooling, the mixture is poured out on 50 ml of water and extracted with 3×50 ml dichloromethane. The aqueous phase is then adjusted to pH 5 with 2N hydrochloric acid and the precipitated solid is suction filtered and recrystallized from methanol.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 3×50 ml dichloromethane
  3. filtrationfiltered
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f692510e22944601972e85efe5669b65
Source dataset
uspto-grants-1990_05
Patent number
US04921856

Reaction notes

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