Lauryldimethylamine → Pyrinuron

HRID 648069

Reaktionsgleichung

Reaktionsgleichung von HRID 648069
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])OC)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.CN(CCCCCCCCCCCC)C>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 8168LauryldimethylamineHCID 310183-PyridinemethanamineHCID 74752Carbamic acid, N-(4-nitrophenyl)-, methyl ester

Produkt 1

HCID 40813PyrinuronAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

196.13 g (1 mole) of methyl N-(4-nitrophenyl)-carbamate, 108.14 g (1 mole) of 3-aminomethyl-pyridine and 106.7 g (0.5 mole) of N,N-dimethyl-n-dodecylamine are dissolved in 3 liters of xylene. The reaction mixture is refluxed, and the spures of water present are removed from the mixture together with the alcohol formed in a Dean-Stark trap. The end-product starts to separate from the mixture within 15-20 minutes from the beginning of boiling. The mixture is boiled for 4 hours, thereafter the suspension is filtered at about 100° to 110° C. The filter cake is washed twice with 100 ml of hot xylene, each, and with a small amount of acetone, and then dried in vacuo. 218.6 g (80.3%) of N-(4-nitrophenyl)-N'-(3-pyridylmethyl)-urea are obtained; m.p.: 221°-223° C.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed
  2. customthe spures of water present are removed from the mixture together with the alcohol
  3. customformed in a Dean-Stark trap
  4. customto separate from the mixture within 15-20 minutes from the beginning of boiling
  5. filtrationthe suspension is filtered at about 100° to 110° C
  6. washThe filter cake is washed twice with 100 ml of hot xylene
  7. dry with materialeach, and with a small amount of acetone, and then dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d3de12e68bde4213939424b23bf92c4f
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410697

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