Phosphorus pentachloride → 4-(4-Chlorosulfonylmethyl-benzyl)-nitrobenzene

HRID 1358825Notes

Reaction equation

HRID 1358825 reaction equation
[Na+].[N+:2]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][S:17]([O-])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].P(Cl)(Cl)(Cl)(Cl)[Cl:24]>O>[Cl:24][S:17]([CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C:8]2[CH:21]=[CH:22][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)=[CH:11][CH:12]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 877141104-(4-Nitrobenzyl)-phenylmethanesulfonic acid sodium salt

Product 1

HCID 218768184-(4-Chlorosulfonylmethyl-benzyl)-nitrobenzeneYield 27.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-(4-Nitrobenzyl)-phenylmethanesulfonic acid sodium salt (2.29 g) was combined with phosphorus pentachloride (1.45 g). The mixture was heated to 90° C. for 5 minutes, poured into water, and extracted with dichloromethane (3×20 mL). Solvents were evaporated to give 4-(4-chlorosulfonylmethylbenzyl)-nitrobenzene as an impure yellow solid (0.63 g). This product was used directly in the next step.

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. customSolvents were evaporated

Sources & evidence

ORD record
ord-5d8d1254e26f4a0bb398792c591a6ef7
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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