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

HRID 972296Notes

Reaction equation

HRID 972296 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-924e0a3816ad40fa845ca4be3654ca0d
Source dataset
uspto-grants-1977_10
Patent number
US04052455

Reaction notes

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