Water → 5-Ethoxy-5-oxopentyl 3,5-bis(acetylamino)-2,4,6-triiodobenzoate

HRID 128889Notes

Reaction equation

HRID 128889 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[C:10]([I:11])=[C:9]([NH:12][C:13]([CH3:15])=[O:14])[C:8]([I:16])=[C:7]([C:17]([O-:19])=[O:18])[C:6]=1[I:20])=[O:3].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C=O)C>[C:13]([NH:12][C:9]1[C:8]([I:16])=[C:7]([C:6]([I:20])=[C:5]([NH:4][C:2](=[O:3])[CH3:1])[C:10]=1[I:11])[C:17]([O:19][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:18])(=[O:14])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 84580Ethyl 5-bromovalerateHCID 23672589Sodium Amidotrizoate

Product 1

HCID 152335965-Ethoxy-5-oxopentyl 3,5-bis(acetylamino)-2,4,6-triiodobenzoateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of sodium diatrizoate (59.0 g, 92.8 mmol) in 350 ml of dry DMF was added ethyl 5-bromovalerate (14.7 ml, 92.8 mmol) in two portions and the resulting solution was stirred at ambient temperature for 12 hr. The reaction mixture was poured into 3.5 1 of water and the resulting white precipitate was collected, washed with ether and then air dried. The crude product was dissolved in acetonitrile-ethanol (5:2), filtered through a pad of silica gel and the filtrate was evaporated to give a solid (67 g, 97%). Recrystallization from methanol-water gave analytically pure product (mp 237°-239° C.) after drying under high vacuum; CI-MS: MH+ 743. The 1H-NMR (300 MHz) spectral data was consistent with the desired product. Calculated for C18H21I3N2O6 ; C 29.13, H 2.85, I 51.30; Found: C 29.13, H 2.78, I 51.15, N 3.75.

Workup

  1. customthe resulting white precipitate was collected
  2. washwashed with ether
  3. customair dried
  4. dissolutionThe crude product was dissolved in acetonitrile-ethanol (5:2)
  5. filtrationfiltered through a pad of silica gel
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c285b02a93bf4c65b4a5dda37d6494de
Source dataset
uspto-grants-1995_11
Patent number
US05466433

Reaction notes

Loading…