Ethyl chloroacetate → Ethyl Cartrizoate

HRID 1108932Notes

Reaction equation

HRID 1108932 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+].Cl[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[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][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:18])(=[O:14])[CH3:15]

Participants

4

Reactant 2

HCID 7751Ethyl chloroacetateHCID 23672589Sodium Amidotrizoate

Product 1

HCID 208939Ethyl CartrizoateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 175 mL of dry N,N-dimethylformamide (DMF) was added 63.6 g (0.100 mol) sodium diatrizoate and 14.7 g (0.120 mol) of ethyl chloroacetate and the mixture was heated on a steam bath for 6 hr. The reaction was filtered while hot and the filtrate cooled to room temperature and diluted to 500 ml with water. The mixture was cooled and filtered and the collected solid washed with water. The solid was then dissolved in 350 ml hot DMF, filtered and added to an equal volume of water. The mixture was cooled, filtered, washed with water, and the solid dried at 100° C. overnight to afford 53.0 g (76% yield) of a white powder, mp 269.5°-270.50° C.

Workup

  1. temperaturethe mixture was heated on a steam bath for 6 hr
  2. filtrationThe reaction was filtered while hot and the filtrate
  3. additiondiluted to 500 ml with water
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washthe collected solid washed with water
  7. dissolutionThe solid was then dissolved in 350 ml hot DMF
  8. filtrationfiltered
  9. additionadded to an equal volume of water
  10. temperatureThe mixture was cooled
  11. filtrationfiltered
  12. washwashed with water
  13. customthe solid dried at 100° C. overnight

Sources & evidence

ORD record
ord-e372a3b393fd4e07975e4983e3b25365
Source dataset
uspto-grants-1994_06
Patent number
US05318768

Reaction notes

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