Acetic Acid → N-phenylmaleamic acid benzyltrimethyl-ammonium salt

HRID 1703740Notes

Reaction equation

HRID 1703740 reaction equation
[OH-].[CH2:2]([N+:9]([CH3:12])([CH3:11])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:13]1([NH:19][C:20](=[O:26])/[CH:21]=[CH:22]\[C:23]([OH:25])=[O:24])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>CO>[CH2:2]([N+:9]([CH3:12])([CH3:11])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:13]1([NH:19][C:20](=[O:26])/[CH:21]=[CH:22]\[C:23]([O-:25])=[O:24])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66854Benzyltrimethylammonium hydroxideHCID 1550938Maleic acid anilide

Product 1

HCID 131711323N-phenylmaleamic acid benzyltrimethyl-ammonium saltYield 108.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

48.2 g (0.1 mole) of benzyltrimethylammonium hydroxide solution (34.7% in methanol) is added to 19.1 g (0.1 mole) of N-phenylmaleamic acid in 100 ml of methanol, and the reaction mixture is stirred for one hour at room temperature. The pH-value is adjusted to about 7.0 with acetic acid, and the solvent is removed in vacuo in a rotary evaporator to leave 36.8 g of N-phenylmaleamic acid benzyltrimethyl-ammonium salt in the form of yellow oil, which crystallises after prolonged standing.

Workup

  1. customthe solvent is removed in vacuo in a rotary evaporator

Sources & evidence

ORD record
ord-ae0d128bcbcc4fb4a9248ecc6adad4e9
Source dataset
uspto-grants-1978_11
Patent number
US04125398

Reaction notes

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