HCID 178510931, compound → HCID 178523905, compound

HRID 1493336Notes

Reaction equation

HRID 1493336 reaction equation
[C:1]([N:9]=[C:10]1[NH:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:23]1[CH:27]=[C:26]([CH2:28][CH2:29][CH2:30][NH2:31])[N:25]=[CH:24]1>C(#N)C.C(O)C>[C:1]([NH:9][C:10]([NH:14][CH2:13][CH:12]([OH:11])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N:31][CH2:30][CH2:29][CH2:28][C:26]1[N:25]=[CH:24][NH:23][CH:27]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 178510931HCID 178510931, compoundHCID 178522538HCID 178522538, compound

Product 1

HCID 178523905HCID 178523905, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

1.48 g (5 mmol) of 2-benzoylimino-5-phenoxymethyloxazolidine and 0.69 g (5.5 mmol) of 3-(imidazole-4-yl)-propylamine are heated together under reflux in a mixture of 40 ml of acetonitrile and 10 ml of ethanol for 8 hours. The reaction mixture is concentrated by evaporation under vacuum and the product is isolated and purified by preparative layer chromatography (silica gel 60 PF254 containing gypsum: solvent; chloroform/methanol 98:2, ammoniacal atmosphere). Crystallisation from acetonitrile results in 0.8 g (38%) of colourless crystals, melting point 129° C.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation under vacuum
  2. customthe product is isolated
  3. custompurified by preparative layer chromatography (silica gel 60 PF254 containing gypsum: solvent; chloroform/methanol 98:2, ammoniacal atmosphere)
  4. customCrystallisation from acetonitrile

Sources & evidence

ORD record
ord-a72ade3b5ae746c8b5f04bedc13177eb
Source dataset
uspto-grants-1991_06
Patent number
US05021431

Reaction notes

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