Hydrochloric Acid → 94319-83-2

HRID 2255105Notes

Reaction equation

HRID 2255105 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.ClC(OCC)=O.[CH2:24]([NH2:27])[CH2:25][NH2:26].Cl>C(Cl)(Cl)Cl>[ClH:8].[NH2:26][CH2:25][CH2:24][NH:27][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[Cl:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 83742-Chlorobenzoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 1302801194319-83-2Yield 108.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

22.1 ml (0.16 mol) of triethylamine are added dropwise at 10° to a suspension of 23.5 g (0.15 mol) of 2-chlorobenzoic acid in 200 ml of chloroform. 14.8 ml (0.155 mol) of ethyl chloroformate are then added dropwise at the same temperature. After completion of the addition (1 hour), the mixture is poured on to ice/water. The chloroform phase is separated, dried over magnesium sulfate and gently concentrated to about 60 ml. The thus-obtained solution is added dropwise at 10° to a solution of 40.1 ml (0.6 mol) of ethylenediamine in 400 ml of chloroform. After completion of the addition, the difficulty soluble neutral constituents are filtered off, the filtrate is concentrated and excess ethylenediamine is removed in a high vacuum. The residue obtained (31.5 g) is converted into the hydrochloride which is purified by recrystallization from ethanol/ether. There are obtained 19.2 g of N-(2-aminoethyl)-2-chlorobenzamide hydrochloride (see Example 6 of German Offenlegungsschrift 2.362.568), m.p. 155°-158°. An analytically pure sample melts at 159°-161°.

Workup

  1. additionAfter completion of the addition (1 hour)
  2. customThe chloroform phase is separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationgently concentrated to about 60 ml
  5. additionAfter completion of the addition
  6. filtrationthe difficulty soluble neutral constituents are filtered off
  7. concentrationthe filtrate is concentrated
  8. customexcess ethylenediamine is removed in a high vacuum
  9. customThe residue obtained (31.5 g)
  10. customis purified by recrystallization from ethanol/ether

Sources & evidence

ORD record
ord-ea63b23d0e124a8ab5b4d4a1c2199940
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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