Hydrochloric Acid → 3-[(2-Chloroacetyl)amino]-alpha-ethyl-2,4,6-triiodobenzenepropanoic acid

HRID 2258387Notes

Reaction equation

HRID 2258387 reaction equation
[NH2:1][C:2]1[C:3]([I:17])=[C:4]([CH2:10][CH:11]([CH2:15][CH3:16])[C:12]([OH:14])=[O:13])[C:5]([I:9])=[CH:6][C:7]=1[I:8].[Cl:18][CH2:19][C:20](Cl)=[O:21].[OH-].[Na+].Cl>CC(N(C)C)=O.O>[Cl:18][CH2:19][C:20]([NH:1][C:2]1[C:3]([I:17])=[C:4]([CH2:10][CH:11]([CH2:15][CH3:16])[C:12]([OH:14])=[O:13])[C:5]([I:9])=[CH:6][C:7]=1[I:8])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3735Iopanoic AcidHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 229213893-[(2-Chloroacetyl)amino]-alpha-ethyl-2,4,6-triiodobenzenepropanoic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 50 g of 3-amino-α-ethyl-2,4,6-triiodobenzenepropanoic acid (CAS RN, 96-83-3) (0.0875 mol) in 200 ml of DMA at 0° C., 11.87 g of chloroacetyl chloride (0.10 mol) are added. After 60 minutes at room temperature, the solution is dropwise added to 100 ml of H2O to give a precipitate which is filtered. The residue is dissolved in 100 ml of H2O and 43.7 ml of 2N NaOH (0.0875 mol) are added. 42 ml of 2N HCl (0.0084 mol) are added to precipitate a solid which is filtered. 5.4 g of 3-[(2-chloroacetyl)amino]-α-ethyl-2,4,6-triiodobenzenepropanoic acid are obtained (0.083 mol).

Workup

  1. customto give a precipitate which
  2. filtrationis filtered
  3. dissolutionThe residue is dissolved in 100 ml of H2O
  4. customto precipitate a solid which
  5. filtrationis filtered

Sources & evidence

ORD record
ord-c5397c9c7a7348e9837ef19d496a2e9a
Source dataset
uspto-grants-1997_08
Patent number
US05660814

Reaction notes

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