Phosphorus pentachloride → 2-[(4-Nitrophenyl)amino]ethanesulfonyl chloride

HRID 1393831Notes

Reaction equation

HRID 1393831 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][S:13]([O-:16])(=O)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:19]>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][S:13]([Cl:19])(=[O:16])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 58586698Sodium 2-(4-nitroanilino)ethanesulfonate

Product 1

HCID 585866722-[(4-Nitrophenyl)amino]ethanesulfonyl chlorideYield 45.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of sodium 2-[(4-nitrophenyl)amino]ethanesulfonate (8) (5.36 g, 0.02 mol), phosphorus pentachloride (4.58 g, 0.022 mol) and 50 mL of anhydrous xylene was heated at about 40-50° C. for 4 hours. After remaining at room temperature overnight, the mixture was heated for 3 hours in a boiling water bath. The resulting mixture was filtered while hot and the insoluble matter was washed three times with hot xylene. The filtrate was left to cool. A yellow solid formed, and was filtered off and reslurried in water. 2.4 g of expected product were isolated.

Workup

  1. temperaturethe mixture was heated for 3 hours in a boiling water bath
  2. filtrationThe resulting mixture was filtered while hot and the insoluble matter
  3. washwas washed three times with hot xylene
  4. waitThe filtrate was left
  5. temperatureto cool
  6. customA yellow solid formed
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-458228c59863449b9d56688e4f70e947
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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