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

HRID 66205

Reaction equation

HRID 66205 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-bd2596347e3e4e34b477f70ffc079fd0
Source dataset
uspto-grants-1978_12
Patent number
US04130663

Linked notes

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