Pent-4-yn-1-amine → N-Cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-N"-(4-pentyn-1-yl)guanidine

HRID 236712

Reaktionsgleichung

Reaktionsgleichung von HRID 236712
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[CH2:18]([NH2:23])[CH2:19][CH2:20][C:21]#[CH:22]>C(#N)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:23][CH2:18][CH2:19][CH2:20][C:21]#[CH:22])#[N:2]

Komponenten

4

Edukt 2

HCID 641001Pent-4-yn-1-amineHCID 178503877HCID 178503877, Verbindung

Produkt 1

HCID 178446439N-Cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-N"-(4-pentyn-1-yl)guanidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of N-cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-S-methylisothiourea (3.00 g., 0.0111 mole) and 4-pentyn-1-amine (3.69 g., 0.0445 mole) in 60 ml. of acetonitrile was stirred at reflux for 24 hours, and then allowed to stand at room temperature for 96 hours. The solvent and excess amine were removed under reduced pressure and the residual yellow gum was purified by chromatography on 50 g. of 100-200 mesh silica gel, using gradient elution with methylene chloride/methanol (99:1-96:4). The middle fractions indicated by TLC to be pure were combined and evaporated to give 1.91 g. of yellow gum which was crystallized at -15° C. from 18 ml. of ethyl acetate. The resulting white solid (1.25 g.) was recrystallized at -15° C. from 10 ml. of acetonitrile to give 1.063 g. of product; m.p. 99°-103° C.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. customThe solvent and excess amine were removed under reduced pressure
  3. customthe residual yellow gum was purified by chromatography on 50 g
  4. washelution with methylene chloride/methanol (99:1-96:4)
  5. customevaporated
  6. customto give 1.91 g
  7. customof yellow gum which was crystallized at -15° C. from 18 ml
  8. customThe resulting white solid (1.25 g.) was recrystallized at -15° C. from 10 ml
  9. customof acetonitrile to give 1.063 g

Quellen und Nachweise

ORD-Eintrag
ord-22909f4230cb4d73965aefc973ee9185
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04157347

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