Ethylenediamine → HCID 86742532, compound

HRID 2231972Notes

Reaction equation

HRID 2231972 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:13]([CH3:18])[C:14]([O:16]C)=O)[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([NH2:22])[CH2:20][NH2:21]>>[NH2:21][CH2:20][CH2:19][NH:22][C:14](=[O:16])[CH:13]([C:7]1[CH:8]=[C:9]([CH3:12])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=1)[CH3:18]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 14454702HCID 14454702, compound

Product 1

HCID 86742532HCID 86742532, compoundYield 84.9%

Procedure

125 g of methyl 3-tert-butyl-4-hydroxy-5-methylphenylpropionate and 300 g of ethylenediamine are heated together at 110° C. for 5 hours, after which a vacuum is applied and the resulting methanol and the excess ethylenediamine are distilled off. 0.3 l of toluene are added to the residue, and the mixture is left to stand at room temperature for one hour. The precipitate is filtered off under suction and dried to give 118 g of the product which, after recrystallization from ethyl acetate, has a melting point of 156°-159° C.

Workup

  1. distillationthe resulting methanol and the excess ethylenediamine are distilled off
  2. addition0.3 l of toluene are added to the residue
  3. waitthe mixture is left
  4. filtrationThe precipitate is filtered off under suction
  5. customdried

Sources & evidence

ORD record
ord-bb9a9076670c45cbbdefe73528c7ed13
Source dataset
uspto-grants-1988_11
Patent number
US04785107

Reaction notes

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