Reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].Cl[CH2:9][C:10]([NH:12][C:13]1[C:14]([I:28])=[C:15]([CH2:21][CH:22]([CH2:26][CH3:27])[C:23]([OH:25])=[O:24])[C:16]([I:20])=[CH:17][C:18]=1[I:19])=[O:11]>>[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:9][C:10]([NH:12][C:13]1[C:14]([I:28])=[C:15]([CH2:21][CH:22]([CH2:26][CH3:27])[C:23]([OH:25])=[O:24])[C:16]([I:20])=[CH:17][C:18]=1[I:19])=[O:11]Participants
Procedure
To 217 g of diethylenetriamine (product commercially available) (2.1 mol), under stirring and under nitrogen atmosphere, 259 g of compound (A) 3-[(2-chloroacetyl) amino]-α-ethyl-2,4,6-triiodobenzenepropanoic acid (0.40 mol) are added. The mixture is kept at 50° C. for 3 h and, after cooling, is extracted with three 500-ml portions of CH2Cl2. After evaporation of the solvent, the residue is dissolved in 500 ml of H2O and acidified with 300 ml of 37% HCl. The resulting solution is counterflow extracted according to Craig with n-BuOH. A residue is obtained, which is purified as trihydrochloride by crystallisation in abs. EtOH after addition of 37% HCl. 187 g of 3-[[[2-[(2-aminoethyl)amino]ethyl]amino]acetylamino]-α-ethyl-2,4,6-triiodobenzenepropanoic acid (0.227 mol) are obtained.
Workup
- temperatureafter cooling
- extractionis extracted with three 500-ml portions of CH2Cl2
- customAfter evaporation of the solvent
- dissolutionthe residue is dissolved in 500 ml of H2O
- extractionextracted
- customA residue is obtained
- customwhich is purified as trihydrochloride by crystallisation in abs
- additionEtOH after addition of 37% HCl
Sources & evidence
- ORD record
- ord-49f14293cea247b5a8680b1ddb1195bd
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05660814
Linked notes
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