Phosphorus pentachloride → 2-(4-Chloro-phenylsulfonylamino)4,5-dimethoxy-benzoyl chloride

HRID 1896965Notes

Reaction equation

HRID 1896965 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14](O)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14]([Cl:26])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 12399912-{[(4-Chlorophenyl)sulfonyl]amino}-4,5-dimethoxybenzoic acid

Product 1

HCID 98433672-(4-Chloro-phenylsulfonylamino)4,5-dimethoxy-benzoyl chlorideYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
42.5 °C

Procedure

25.90 g (0.07 mol) of 2-(4-chloro-phenylsulfonylamino)-4,5-dimethoxy-benzoic acid were mixed with 75 ml of toluene, 17.30 g (0.08 mol) of phosphorus pentachloride were added and the mixture was stirred at 40-45° C. for 2.5 h. Then the mixture was concentrated in vacuo to half of its volume and the product that precipitated was filtered off with suction and washed with a small amount of toluene. 25.30 g (93%) of 2-(4-chloro-phenylsulfonylamino)-4,5-dimethoxy-benzoyl chloride having a melting point of 175-177° C. were obtained.

Workup

  1. additionwere added
  2. concentrationThen the mixture was concentrated in vacuo to half of its volume
  3. customthe product that precipitated
  4. filtrationwas filtered off with suction
  5. washwashed with a small amount of toluene

Sources & evidence

ORD record
ord-c5e542d974ec4b5592f569bb375497bc
Source dataset
uspto-grants-2013_08
Patent number
US08518998B2

Reaction notes

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