Ethylenediamine → 3560-43-8

HRID 2255107Notes

Reaction equation

HRID 2255107 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:19]C(OCC)=O.[CH2:25]([NH2:28])[CH2:26][NH2:27]>C(Cl)(Cl)Cl>[ClH:19].[NH2:27][CH2:26][CH2:25][NH:28][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 74784-Methoxybenzoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 197417633560-43-8Yield 36.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 6.4 g (0.04 mol) of 4-methoxybenzoic acid in 60 ml of chloroform are added dropwise at 10°, 5.5 ml (0.04 mol) of triethylamine and then 3.8 ml (0.04 mol) of ethyl chloroformate. The solution obtained is then added dropwise at 5° to a solution of 10.7 ml (0.16 mol) of ethylenediamine in 100 ml of chloroform. After stirring at room temperature for 2 hours, the mixture is filtered. The filtrate is concentrated under reduced pressure and then excess ethylenediamine is removed in a high vacuum. The residue is acidified with dilute hydrochloric acid and extracted several times with ethyl acetate. The aqueous phase is made alkaline with 28% sodium hydroxide solution and extracted three times with chloroform. After drying and concentrating the chloroform extracts, the residue is converted into the hydrochloride. By recrystallization from ethanol/ether there are obtained 3.4 g of N-(2-aminoethyl)-4-anisamide hydrochloride (see Example 7 of German Offenlegungsschrift 2.616.486), m.p. 186°-189°. The free base melts at 37°-38°.

Workup

  1. additionare added dropwise at 10°
  2. customThe solution obtained
  3. filtrationthe mixture is filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customexcess ethylenediamine is removed in a high vacuum
  6. extractionextracted several times with ethyl acetate
  7. extractionextracted three times with chloroform
  8. customAfter drying
  9. concentrationconcentrating the chloroform
  10. customBy recrystallization from ethanol/ether there

Sources & evidence

ORD record
ord-338ed93d2f52405aad062e77b7082bb5
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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