Bromoacetyl bromide → HCID 86606426, compound

HRID 131991Notes

Reaction equation

HRID 131991 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][NH2:23])[C:5](=[O:20])[C:6]1[C:14]([I:15])=[C:13]([NH:16][CH3:17])[C:12]([I:18])=[C:8]([C:9]([OH:11])=[O:10])[C:7]=1[I:19].[Br:24][CH2:25][C:26](Br)=[O:27]>CC(N(C)C)=O>[Br:24][CH2:25][C:26]([NH:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][NH:23][C:26](=[O:27])[CH2:25][Br:24])[C:5](=[O:20])[C:6]1[C:14]([I:15])=[C:13]([NH:16][CH2:17][C:26](=[O:27])[CH2:25][Br:24])[C:12]([I:18])=[C:8]([C:9]([OH:11])=[O:10])[C:7]=1[I:19])=[O:27]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 86606425HCID 86606425, compound2×

Product 1

HCID 86606426HCID 86606426, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
40 °C

Procedure

50 g (76.1 mmol) of N,N-bis-(2-aminoethyl)-5-(methylamino)-2,4,6-triiodoisophthalic acid amide (title compound 1a) is dissolved in 500 ml of dimethylacetamide, and at 0° C., 70.6 g (350 mmol) of bromoacetyl bromide (Aldrich) is added in drops over 15 minutes. Then, it is stirred for 20 hours at 40° C. The reaction mixture is poured into 4000 ml of ice water, the accumulating solid is filtered off, dissolved in 800 ml of ethyl acetate and extracted three times with 250 ml each of water. The organic phase is dried on sodium sulfate, and the solvent is evaporated to the dry state. The crude product is recrystallized from methyl-tert-butyl ether.

Workup

  1. filtrationthe accumulating solid is filtered off
  2. dissolutiondissolved in 800 ml of ethyl acetate
  3. extractionextracted three times with 250 ml each of water
  4. customThe organic phase is dried on sodium sulfate
  5. customthe solvent is evaporated to the dry state
  6. customThe crude product is recrystallized from methyl-tert-butyl ether

Sources & evidence

ORD record
ord-78250dd4415b47618063863a86dff97a
Source dataset
uspto-grants-2008_06
Patent number
US07385054B2

Reaction notes

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