Triethylamine → 5-(3-Methoxyphenyl)benzimidazolidin-2-one

HRID 413248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413248
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([NH2:18])=[C:13]([CH:17]=2)C(O)=O)[CH:6]=[CH:7][CH:8]=1.C[N:20]1CCC[C:21]1=[O:25].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[NH:18][C:21](=[O:25])[NH:20][C:13]=3[CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 223253354-Amino-3'-methoxy[1,1'-biphenyl]-3-carboxylic acid

Produkt 1

HCID 223253275-(3-Methoxyphenyl)benzimidazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 5-(3-methoxyphenyl)-2-aminobenzoic acid (2.0g) in 1,4-dioxane (20 mL) add N-methylpyrolidinone (NMP, 5 mL) and triethylamine (1.4 mL), followed by diphenyl phosphoric azide (DPPA, 2.5 g). After stirring at ambient temperature for 30 minutes, heat the mixture to 100° C. for 2 hours, until gas evolution fully subsided. Cool the mixture to ambient temperature and concentrate in vacuo. Dissolve the residue in MeOH and leave to stand for 18 hours. Filter the precipitate and air dry to obtain 5-(3-methoxyphenyl)benzimidazolidin-2-one as a pale yellow solid.

Aufarbeitung

  1. temperatureheat the mixture to 100° C. for 2 hours
  2. temperatureCool the mixture to ambient temperature
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in MeOH
  5. customleave
  6. waitto stand for 18 hours
  7. filtrationFilter the precipitate and air
  8. customdry

Quellen und Nachweise

ORD-Eintrag
ord-8b709cc66827410b9b2df21321afb77d
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566367B2

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