Sodium Hydroxide → 1,4-Bis(m-carboxyphenylsulfonyl)-2,5-dimethylpiperazine

HRID 437732

Reaction equation

HRID 437732 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][NH:3]1.Cl[S:10]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17])(=[O:12])=[O:11].[OH-:22].[Na+]>O>[C:16]([C:15]1[CH:14]=[C:13]([S:10]([N:3]2[CH2:4][CH:5]([CH3:8])[N:6]([S:10]([C:13]3[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([OH:18])=[O:17])[CH:14]=3)(=[O:11])=[O:22])[CH2:7][CH:2]2[CH3:1])(=[O:12])=[O:11])[CH:21]=[CH:20][CH:19]=1)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 2206722,5-Dimethylpiperazine, trans-

Product 1

HCID 214268161,4-Bis(m-carboxyphenylsulfonyl)-2,5-dimethylpiperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Binder 15 was prepared as follows: Trans-2,5-dimethylpiperazine in water at 50° C. was treated with slightly more than two molar equivalents of m-chlorosulfonylbenzoic acid and five molar equivalents of aqueous sodium hydroxide. Acidification gave 1,4-bis(m-carboxyphenylsulfonyl)-2,5-dimethylpiperazine which was recrystallized from aqueous ethanol. The dimethyl ester was made by boiling the acid for 24 hours in methanol to which some hydrogen chloride has been added. Recrystallization from 2:1 dioxane: water gave a product which melted at 223°-227° C. Anal. Calc'd for C22H26N2O8S2 : C, 51.7; H, 5.1; N, 5.5. Found: C, 51.6; H, 5.4; N, 5.7. The polymer was then made from this ester and ethylene glycol as described for Binder 6.

Workup

  1. customBinder 15 was prepared

Sources & evidence

ORD record
ord-a7ecdcd3e92647caa616e5f9ba1ee681
Source dataset
uspto-grants-1977_06
Patent number
US04032344

Linked notes

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