Propanoyl bromide, 2-bromo- → HCID 86606427, compound

HRID 131992Notes

Reaction equation

HRID 131992 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:20][CH2:21][NH2:22])[C:5](=[O:19])[C:6]1[C:14]([I:15])=[C:13]([NH2:16])[C:12]([I:17])=[C:8]([C:9]([OH:11])=[O:10])[C:7]=1[I:18].[Br:23][CH:24]([CH3:28])[C:25](Br)=[O:26]>CC(N(C)C)=O>[Br:23][CH:24]([CH3:28])[C:25]([NH:1][CH2:2][CH2:3][N:4]([CH2:20][CH2:21][NH:22][C:25](=[O:26])[CH:24]([Br:23])[CH3:28])[C:5](=[O:19])[C:6]1[C:14]([I:15])=[C:13]([NH:16][C:25](=[O:26])[CH:24]([Br:23])[CH3:28])[C:12]([I:17])=[C:8]([C:9]([OH:11])=[O:10])[C:7]=1[I:18])=[O:26]

Participants

4

Reactant 2

HCID 79047Propanoyl bromide, 2-bromo-HCID 86606428HCID 86606428, compound

Product 1

HCID 86606427HCID 86606427, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
40 °C

Procedure

50 g (77.8 mmol) of N,N-bis-(2-aminoethyl)-5-amino-2,4,6-triiodoisophthalic acid amide is dissolved in 500 ml of dimethylacetamide, and 75.5 g (350 mmol) of 2-bromopropionic acid bromide (Aldrich) is added in drops over 15 minutes at 0° C. 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-5152a5a95fcd4076bdc52e86b1deb0f2
Source dataset
uspto-grants-2008_06
Patent number
US07385054B2

Reaction notes

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