Diethyl Ether → 2,4,6-Triiodo-1,3,5-tris-(aminoethoxymethyl)benzene
Reaction equation
[I:1][C:2]1[C:7]([CH2:8][O:9][CH2:10][CH2:11][NH:12]C(OC(C)(C)C)=O)=[C:6]([I:20])[C:5]([CH2:21][O:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)=[C:4]([I:33])[C:3]=1[CH2:34][O:35][CH2:36][CH2:37][NH:38]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.C(OCC)C.[OH-].[Na+]>ClCCl.O>[I:1][C:2]1[C:3]([CH2:34][O:35][CH2:36][CH2:37][NH2:38])=[C:4]([I:33])[C:5]([CH2:21][O:22][CH2:23][CH2:24][NH2:25])=[C:6]([I:20])[C:7]=1[CH2:8][O:9][CH2:10][CH2:11][NH2:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
24.4 g (25 mmol) of 2,4,6-triiodo-1,3,5-tris-(2-tert-butoxycarbonylaminoethoxymethyl)benzene is dissolved in 100 ml of dichloromethane, mixed at 0° C. with 100 ml of trifluoroacetic acid and stirred for 3 hours at 0° C. The batch is poured into 500 ml of diethyl ether, the solid that accumulates in this case is suctioned off and rewashed several times with diethyl ether. The residue is dissolved in 100 ml of water and 100 ml of dichloromethane while being stirred vigorously, and 32% NaOH solution is added until a pH of 10 is reached. The organic phase is separated, the aqueous phase is extracted three times with 50 ml each of dichloromethane, the combined organic phases are dried on magnesium sulfate and evaporated to the dry state.
Workup
- customThe organic phase is separated
- extractionthe aqueous phase is extracted three times with 50 ml each of dichloromethane
- customthe combined organic phases are dried on magnesium sulfate
- customevaporated to the dry state
Sources & evidence
- ORD record
- ord-2a0584e5107a4ab896d189fb059aa205
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07208140B2
Reaction notes
Loading…