Ethylenediamine → HCID 13576897, compound

HRID 2255104Notes

Reaction equation

HRID 2255104 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH2:25]([NH2:28])[CH2:26][NH2:27]>C(Cl)Cl.O1CCCC1>[ClH:1].[NH2:27][CH2:26][CH2:25][NH:28][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[Cl:1]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 57872,4-Dichlorobenzoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 13576897HCID 13576897, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

19.1 g (0.1 mol) of 2,4-dichlorobenzoic acid are suspended in 200 ml of methylene chloride and brought into solution by adding 15.3 ml (0.11 mol) of triethylamine. 10 ml (0.1 mol) of ethyl chloroformate are then added dropwise at 0°. After completion of the addition (0.5 hour), the mixture is poured on to ice/water. The methylene chloride phase is separated, dried over magnesium sulfate and concentrated to about 30 ml. This solution is added dropwise at 0° to a solution of 20 ml (0.3 mol) of ethylenediamine in 100 ml of tetrahydrofuran. After completion of the addition (0.5 hour), the mixture is filtered, the filtrate is acidified with dilute hydrochloric acid the neutral constituents are removed by extraction with ethyl acetate. The aqueous phase is made alkaline with sodium hydroxide solution and extracted several times with chloroform. After drying and concentrating the chloroform phases, the residue is converted into the hydrochloride. After recrystallization from ethanol/ether, there are obtained 7.1 g of N-(2-aminoethyl)-2,4-dichlorobenzamide hydrochloride, m.p. 179°-182°.

Workup

  1. additionAfter completion of the addition (0.5 hour)
  2. customThe methylene chloride phase is separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to about 30 ml
  5. additionAfter completion of the addition (0.5 hour)
  6. filtrationthe mixture is filtered
  7. customare removed by extraction with ethyl acetate
  8. extractionextracted several times with chloroform
  9. customAfter drying
  10. concentrationconcentrating the chloroform phases
  11. customAfter recrystallization from ethanol/ether, there

Sources & evidence

ORD record
ord-5f7802d8a01349f4b958b4a86ce0f6ff
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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