Thionyl Chloride → 2-(4-Ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrobenzyl chloride

HRID 2107591Notes

Reaction equation

HRID 2107591 reaction equation
[F:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]2)=[C:4]([C:7]([F:13])=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5]O.S(Cl)([Cl:27])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:3]2[C:2]([F:1])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([F:13])[C:4]=2[CH2:5][Cl:27])[CH2:15][CH2:16]1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 156225283,6-Difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrobenzyl alcohol

Product 1

HCID 156318302-(4-Ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrobenzyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3,6-difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrobenzyl alcohol (8.5 g) in chloroform (85 ml) is added thionyl chloride (2.7 ml) at room temperature. The mixture is stirred at the same temperature for 30 minutes, and the reaction mixture is poured into ice water, and then neutralized with sodium hydrogen carbonate and extracted with diethyl ether. The extract is dried over magnesium sulfate, and then the solvent is distilled off to give 2-(4-ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrobenzyl chloride (8.1 g).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract is dried over magnesium sulfate
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-1d2cf0ff893449f893c018e3b77c1531
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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