Phosgene → N-pentyl-N-phenylcarbamoyl chloride

HRID 486749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486749
[CH2:1]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].[C:15](Cl)([Cl:17])=[O:16]>C1(C)C=CC=CC=1>[CH2:1]([N:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:15]([Cl:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 3

HCID 6371Phosgene2×HCID 14798Sodium HydroxideHCID 75865N-Pentylaniline

Produkt 1

HCID 18965165N-pentyl-N-phenylcarbamoyl chlorideAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 4.05 g (24.8 mmole) of N-Pentylaniline (from Step A) in 45 ml of toluene an 8.96 ml (24.8 mmole) of 2.77N NaOH were mechanically stirred at -5° C., and 25.7 ml (49.6 mmole) of 1.93M phosgene in toluene was added dropwise over 30 minutes while maintaining -5°. After half the phosgene solution had been added, the rate of addition was increased easily. After stirring at -5° for an additional 30 minutes, the phases were separated and the toluene layer was dried over 10 g of solid sodium chloride. Concentration gave 5.5 g (98%) of dark yellow oil.

Aufarbeitung

  1. temperaturewhile maintaining -5°
  2. additionthe rate of addition
  3. temperaturewas increased easily
  4. customthe phases were separated
  5. dry with materialthe toluene layer was dried over 10 g of solid sodium chloride
  6. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-9ca3b2c3f5464eb8817b2232083787af
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292726

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