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

HRID 1638666Notes

Reaction equation

HRID 1638666 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 mintues, 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-5f4dfdf962a74a529719c5865f673925
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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