1-Hydroxybenzotriazole → 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 1-hydroxybenzotriazole

HRID 1785389Notes

Reaction equation

HRID 1785389 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10][CH3:11].[OH:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1>ClCCl>[OH:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1.[ClH:1].[CH3:12][N:3]([CH3:2])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 865980741-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 1-hydroxybenzotriazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The acid (1.2 eq.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 eq.) and 1-hydroxybenzotriazole (1.2 eq.) were dissolved in 20 volumes of dichloromethane and the solution stirred for 5 min at room temperature. A solution of the amine E (1 eq.) in 10 volumes dichloromethane was added to the mixture, which was stirred at room temperature overnight. The solution was washed with saturated aqueous NaHCO3, dried over Na2SO4 and filtered. The dichloromethane was removed in vacuo to give the products which were purified with appropriate eluants as shown below.

Workup

  1. stirringwas stirred at room temperature overnight
  2. washThe solution was washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe dichloromethane was removed in vacuo
  6. customto give the products which
  7. customwere purified with appropriate eluants

Sources & evidence

ORD record
ord-5f48bf5a11d14a35a148d2be9dc00330
Source dataset
uspto-grants-2009_03
Patent number
US07504506B2

Reaction notes

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