Dimethylformamide → HCID 178446844, Verbindung

HRID 865382

Reaktionsgleichung

Reaktionsgleichung von HRID 865382
Cl.[C:2](=[NH:9])(OC)[CH2:3][CH2:4][CH2:5][CH3:6].CN(C)C=O.[NH2:15][CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1>C(N(CC)CC)C>[NH:9]=[C:2]([NH:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:24][CH:25]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 655264-(Aminomethyl)Benzoic AcidHCID 5743465Methyl valerimidate hydrochloride

Produkt 1

HCID 178446844HCID 178446844, VerbindungAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A 22 L, three-necked round bottom flask equipped with an air-powered mechanical stirrer was placed under a nitrogen atmosphere. The vessel was charged with methyl valerimidate hydrochloride (2.5 kg, 16 mol) and dimethylformamide (9.2 L). A thermometer was attached and the suspension cooled to 0°-15° C. with a cooling bath. Triethylamine (2.3 L) was added to the reaction at such a rate so that the internal temperature did not exceed 25° C. The cooling was stopped and the reaction was allowed to stir 1 hour. The reaction mixture was vacuum filtered using a Buchner funnel and a carboy (20 L). The filter cake was washed with additional dimethylformamide (1.0 L) and force-air dried for 15 min. The combined filtrates were saved. Another clean 22 L, three-necked round bottom flask equipped as above was placed under nitrogen. The vessel was charged with the combined filtrates from above followed by triethylamine (1.6 L) and 4-(aminomethyl)benzoic acid (1.7 kg, 11.5 mol). The thermometer was attached and the suspension was heated to an internal temperature of 65° C. with a heating mantle and a temperature controller. The heating was continued for 20 hours. The reaction was cooled to ambient temperature and filtered to yield 2.5 kg of product; 92% uncorrected yield.

Aufarbeitung

  1. customA 22 L, three-necked round bottom flask equipped with an air-powered mechanical stirrer
  2. temperaturethe suspension cooled to 0°-15° C. with a cooling bath
  3. customdid not exceed 25° C
  4. filtrationfiltered
  5. washThe filter cake was washed with additional dimethylformamide (1.0 L)
  6. customforce-air dried for 15 min
  7. customAnother clean 22 L, three-necked round bottom flask equipped
  8. additionThe vessel was charged with the combined filtrates
  9. waitThe heating was continued for 20 hours
  10. temperatureThe reaction was cooled to ambient temperature
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c3a0ea997fa143a9be2c59079e4f8f23
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565577

Verknüpfte Notizen

Wird geladen…