Phosphorus pentachloride → N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzimidoyl chloride

HRID 128422

Reaction equation

HRID 128422 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH:5]=[CH:6][S:7]([NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=[O:9])=[O:8].P(Cl)(Cl)(Cl)(Cl)[Cl:28]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH:5]=[CH:6][S:7]([N:10]=[C:11]([Cl:28])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 54226549N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzamide

Product 1

HCID 54107493N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzimidoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzamide (8.3 g., 0.02 mole) in 100 ml. of dry benzene is stirred and refluxed with phosphorus pentachloride (4.6 g., 0.022 mole) for a period of 1.5 hr. providing a clear solution which is concentrated under reduced pressure. Benzene is added to the residue and evaporated. The benzene treatment is repeated several times and the residue thus obtained triturated with isopropyl ether provides a quantitative yield of N-(3,4-dichlorostyrylsulfonyl)-3,4-dimethoxybenzimidoyl chloride, m.p. 120°-125° C.

Workup

  1. customproviding a clear solution which
  2. concentrationis concentrated under reduced pressure
  3. additionBenzene is added to the residue
  4. customevaporated
  5. customthe residue thus obtained
  6. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-59f2c37ef9c249e0abe35eebf7f71278
Source dataset
uspto-grants-1981_03
Patent number
US04259482

Linked notes

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