Carbon Dioxide → HCID 178457589, Verbindung

HRID 1770073

Reaktionsgleichung

Reaktionsgleichung von HRID 1770073
[CH:1]([NH2:4])([CH3:3])[CH3:2].C(=O)=O.Cl.[N-:9]([C:12]#[N:13])[C:10]#[N:11].[Na+]>C(O)CCC.CC(C)=O>[C:10]([NH:9][C:12]([NH:4][CH:1]([CH3:3])[CH3:2])=[NH:13])#[N:11]

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 4350929Sodium dicyanamide

Produkt 1

HCID 178457589HCID 178457589, VerbindungAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 2631-ButanolLösungsmittel

Versuchsvorschrift

All the above-named compounds except N-[1-(9,10 dihydro-9,10 dioxo)anthracenyl]-N'-(1-methylethyl)imido dicarbonimidic diamide hydrochloride are commercially available. N-[1-(9,10 dihydro-9,10 dioxo)anthracenyl]-N'-(1-methylethyl)imido dicarbonimidic diamide hydrochloride, however, is a novel compound and was synthesized as follows: A three liter round bottomed flask was charged with 18.2 g (3.09 mole) of isopropyl amine. After cooling the flask to -70° C. in a dry ice and acetone bath, 304.5 g of concentrated (37%) hydrochloric acid (3.09 mole) was added. The mixture was warmed to room temperature and water was removed with a rotary evaporator at aspirator pressure. To the dry residue was added 275.3 g (3.09 mole) of sodium dicyanamide and 760 ml of 1-butanol. The mixture was heated under reflux for three hours and then the butanol was removed with a rotary evaporator at aspirator pressure. To the residue in the flask was added 1800 ml of 1,4-dioxane. A slightly sticky precipitate was formed which was filtered and recrystallized from four liters of 1,4-dioxane to yield 379 g of N-cyano-N'-isopropylguanidine as a co-precipitate with some NaCl, 1,4-dioxane, and isopropylamine. Calc. for C5H10N4 (NaCl)0.1(C4H8O2)0.1(C3H9N)0.15 Calc: C 46.94; H 8.18; N 38.83; C12.37 Found: C 46.85; H 8.27; N 38.42; Cl 2.44

Aufarbeitung

  1. customwas synthesized
  2. additionwas added
  3. customwater was removed with a rotary evaporator at aspirator pressure
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for three hours
  6. customthe butanol was removed with a rotary evaporator at aspirator pressure
  7. additionTo the residue in the flask was added 1800 ml of 1,4-dioxane
  8. customA slightly sticky precipitate was formed which
  9. filtrationwas filtered
  10. customrecrystallized from four liters of 1,4-dioxane

Quellen und Nachweise

ORD-Eintrag
ord-5c368781f5a84581a7942093343179d8
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05385842

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