Phosphorus oxychloride → N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzamide

HRID 66204

Reaktionsgleichung

Reaktionsgleichung von HRID 66204
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH:5]=[CH:6][S:7]([NH2:10])(=[O:9])=[O:8].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21].P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH:5]=[CH:6][S:7]([NH:10][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:17]([O:16][CH3:15])[CH:18]=1)(=[O:8])=[O:9]

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 77070Veratroyl chlorideHCID 537943803,4-Dichlorostyrylsulfonamide

Produkt 1

HCID 54226549N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzamideAusbeute 70 %

Versuchsvorschrift

A mixture of 3,4-dichlorostyrylsulfonamide (12.6 g., 0.05 mole) and 3,4-dimethoxybenzoyl chloride (11.0 g., 0.055 mole) in 15 ml. of phosphorus oxychloride is heated at steam bath temperature for a period of 30 min. Excess phosphorus oxychloride is removed under reduced pressure and dry benzene added. The benzene is evaporated and the treatment repeated two times. Benzene (50 ml.) is added to the residue thus obtained and the insoluble solid collected providing 14.6 g. (70% yield) of N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzamide, m.p. 145°-147° C.

Aufarbeitung

  1. customExcess phosphorus oxychloride is removed under reduced pressure and dry benzene
  2. additionadded
  3. customThe benzene is evaporated
  4. additionBenzene (50 ml.) is added to the residue
  5. customthus obtained
  6. customthe insoluble solid collected
  7. customproviding 14.6 g

Quellen und Nachweise

ORD-Eintrag
ord-d3085db84eba49a1aa3fa73c1acc3e62
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04130663

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