Phosphorus pentachloride → 2-(3-Nitrobenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

HRID 2182839Notes

Reaction equation

HRID 2182839 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].P(Cl)(Cl)(Cl)(Cl)Cl.[N+:20]([C:23]1[CH:24]=[C:25]([S:29]([CH2:32][CH2:33]O)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21]>O>[N+:20]([C:23]1[CH:24]=[C:25]([S:29]([CH2:32][CH2:33][O:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:6]=2)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-

Product 1

HCID 713766552-(3-Nitrobenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To solid 3-chlorosulfonylbenzoic acid (3.2 g, 14.4 mmol) was added solid PCl5 (3.0 g, 14.4 mmol) at room temperature with mixing. The mixture was heated to 70° C. forming a brown liquid that was heated for an additional 2 h. POCl3 side product was removed by vacuum distillation and the residual brown oil was dissolved in 15 mL of CH3CN, and then 2-(3-nitrobenzenesulfonyl)ethanol (2.8 g, 12.0 mmol) was added. The mixture was heated to reflux temperature for 36 h. Thereafter water was added and the mixture was extracted with CH2Cl2. The resulting oil was purified by short column chromatography (eluent: CH2Cl2 to 1% MeOH in CH2Cl2) to give a brown semisolid, which became a white solid by treatment with ether-EtOAc (yield 2.75 g (53%)).

Workup

  1. additionwith mixing
  2. customforming a brown liquid that
  3. temperaturewas heated for an additional 2 h
  4. customPOCl3 side product was removed by vacuum distillation
  5. dissolutionthe residual brown oil was dissolved in 15 mL of CH3CN
  6. temperatureThe mixture was heated
  7. temperatureto reflux temperature for 36 h
  8. extractionthe mixture was extracted with CH2Cl2
  9. customThe resulting oil was purified by short column chromatography (eluent: CH2Cl2 to 1% MeOH in CH2Cl2)
  10. customto give a brown semisolid, which

Sources & evidence

ORD record
ord-bda2d8a652764b05887a848632272e3b
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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