Benzene, 1-isocyanato-4-nitro- → 1-chloro-2-(N-4-nitrophenylcarbamoyloxy)-2-methoxyiminoethane

HRID 1578599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1578599
[CH3:1][O:2][NH:3][C:4](=[O:7])[CH2:5][Cl:6].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1)([O-:10])=[O:9]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:6][CH2:5][C:4]([O:7][C:18](=[O:19])[NH:17][C:14]1[CH:13]=[CH:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:16][CH:15]=1)=[N:3][O:2][CH3:1]

Komponenten

5

Edukt 2

HCID 66012Benzene, 1-isocyanato-4-nitro-HCID 127743452-chloro-N-methoxyacetamide

Produkt 1

HCID 867330531-chloro-2-(N-4-nitrophenylcarbamoyloxy)-2-methoxyiminoethane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9809426Di-n-butyldilauryltinKatalysatorHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (80 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. 4-Nitrophenylisocyanate (16.4 grams; 0.1 mole) dissolved in benzene (30 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 4 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-(N-4-nitrophenylcarbamoyloxy)-2-methoxyiminoethane.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionis incrementally added to the reaction mixture
  4. additionAfter the addition
  5. temperatureis heated
  6. temperatureat reflux for a period of about 4 hours
  7. distillationAfter this time the reaction mixture is distilled
  8. customto remove benzene

Quellen und Nachweise

ORD-Eintrag
ord-966a7a40031b40ec84318b1c0dc7745d
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03937824

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