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Methyl chloroformate → 5-[3-(N-ethylanilinocarbonyl)propoxy]-3,4-dihydrocarbostyril

HRID 1154936
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1154936
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:18])[NH:13]2)([OH:3])=O.CN1CCOCC1.ClC(OC)=O.[CH2:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32]>O.C(Cl)Cl>[CH2:31]([N:33]([C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:18])[NH:13]2)=[O:3])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6586Methyl chloroformateHCID 7670N-EthylanilineHCID 79724-MethylmorpholineHCID 12819301HCID 12819301, Verbindung

Produkt 1

HCID 132003195-[3-(N-ethylanilinocarbonyl)propoxy]-3,4-dihydrocarbostyril

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.5 Grams of 5-(3-carboxy)propoxy-3,4-dihydrocarbostyril and 2.0 ml of N-methylmorpholine are added to 200 ml of methylene chloride, and then 1.0 ml of methyl chloroformate is added dropwise to said solution under external ice cooling and agitation while maintaining the internal temperature at 10°-20° C. After this dropwise addition, the mixture is further agitated at room temperature for 30 minutes and then added with 1.3 ml of N-ethylaniline, followed by additional 4-hour agitation at the same temperature. After the reaction, the reaction solution is added with water, and after liquid separation, the organic layer is washed with a dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order and then dried with anhydrous Na2SO4. After filtering out the inorganic matter, the mother liquor is concentrated and the residue is recrystallized from ethanol, consequently obtaining 2.6 g of 5-[3-(N-ethylanilinocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. m.p. 179.5°-180.5° C.

Aufarbeitung

  1. temperatureagitation while maintaining the internal temperature at 10°-20° C
  2. additionAfter this dropwise addition
  3. waitfollowed by additional 4-hour
  4. customAfter the reaction
  5. customafter liquid separation
  6. washthe organic layer is washed with a dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order
  7. dry with materialdried with anhydrous Na2SO4
  8. filtrationAfter filtering out the inorganic matter
  9. concentrationthe mother liquor is concentrated
  10. customthe residue is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-60349dc66b1046e7bd435f515d7bbf8f
Quelldatensatz
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04298739

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