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

HRID 839565Notes

Reaction equation

HRID 839565 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 phosphorous oxychloride is heated at steam bath temperature for a period of 30 min. Excess phosphorous 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 phosphorous 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-0a15fc7bd2d048ca9e14889a25efed1f
Source dataset
uspto-grants-1978_06
Patent number
US04096183

Reaction notes

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