Ethylenediamine → HCID 19424597, compound

HRID 743498Notes

Reaction equation

HRID 743498 reaction equation
[CH2:1]1[N:8]([CH2:9][CH2:10][NH+:11]([CH2:22][C:23]([O-:25])=[O:24])[CH2:12][CH2:13][N:14]2[CH2:21][C:19](=[O:20])[O:18][C:16](=[O:17])[CH2:15]2)[CH2:7][C:5](=[O:6])[O:4][C:2]1=[O:3].[NH2:26][CH2:27][CH2:28][NH2:29]>CS(C)=O.CS(C)=O.C1CN2C(=NCCC2)C1>[C:16]([CH2:15][N:14]1[CH2:21][C:19](=[O:20])[NH:29][CH2:28][CH2:27][NH:26][C:2](=[O:3])[CH2:1][N:8]([CH2:7][C:5]([OH:4])=[O:6])[CH2:9][CH2:10][N:11]([CH2:22][C:23]([OH:25])=[O:24])[CH2:12][CH2:13]1)([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 1676040123911-26-4

Product 1

HCID 19424597HCID 19424597, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 69529545HCID 69529545, compoundSolvent

Procedure

A 500 mL three-neck flash was charged with 150 mL of dry DMSO and the flask flushed with nitrogen. Two syringes were charged separately with solutions of diethylenetriaminepentaacetic acid dianhydride (2.00 g, 5.60 mmol) in 125 mL of DMSO, and 1,2-diaminoethane (0.336 g, 5,60 mmol) in DMSO/DBN (122 mL/3 mL). The solutions were added simultaneously to the flask at ambient temperature at a rate of 40 mL/hour. After the addition was complete, the reaction mixture was allowed to stir for 48 hours, concentrated under vacuum to 10 mL and 5 mL of water added. This solution, at pH 10.9, was applied to AG1-X8 (100-200 mesh, OAc-) resin, and the column eluted with 0.5N acetic acid to yield 0.71 g (30%) product as a white solid after acetic acid removal and lyophilization.

Workup

  1. customthe flask flushed with nitrogen
  2. additionThe solutions were added simultaneously to the flask at ambient temperature at a rate of 40 mL/hour
  3. additionAfter the addition
  4. concentrationconcentrated under vacuum to 10 mL and 5 mL of water
  5. additionadded
  6. washthe column eluted with 0.5N acetic acid

Sources & evidence

ORD record
ord-a2f52316b4a94c39abe2ea8b3fbe1e82
Source dataset
uspto-grants-1996_09
Patent number
US05556968

Reaction notes

Loading…