Guanidine Hydrochloride → HCID 18945440, Verbindung

HRID 399870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399870
[I-].ClC1C=CC=C[N+]=1C.[C:10]([C:12]1[CH:13]=[C:14]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH:15]=[C:16]([CH:20]=1)[C:17]([OH:19])=O)#[N:11].Cl.[NH2:27][C:28]([NH2:30])=[NH:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:10]([C:12]1[CH:13]=[C:14]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH:15]=[C:16]([CH:20]=1)[C:17]([N:27]=[C:28]([NH2:30])[NH2:29])=[O:19])#[N:11]

Komponenten

10

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 1670692-Chloro-1-methylpyridinium iodideHCID 18945142HCID 18945142, Verbindung

Produkt 1

HCID 18945440HCID 18945440, VerbindungAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Chloro-1-methylpyridinium iodide (3.6 g) was added to a mixture of 5-cyano-3-(pyrrol-1-yl)benzoic acid (2.0 g), guanidine hydrochloride (2.7 g) and triethylamine (7.2 ml) in N,N-dimethylformamide (30 ml), and the mixture was stirred for 4 hours at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate, tetrahydrofuran and water, and adjusted to pH 10 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with ether to give 2-[5-cyano-3-(pyrrol-1-yl)benzoyl]guanidine (1.49 g).

Aufarbeitung

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed by concentration
  4. customthe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-156620907c0947a4aac9e70f4121b764
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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