Hydrochloric Acid → 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)adipanilic acid

HRID 1763284Notes

Reaction equation

HRID 1763284 reaction equation
[C:1]([C:4]1[C:5]([I:28])=[C:6]([C:18]([I:27])=[C:19]([N:22]([CH3:26])[C:23](=[O:25])[CH3:24])[C:20]=1[I:21])[NH:7][C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])([OH:3])=[O:2].[OH-].[Na+].Cl>O>[C:1]([C:4]1[C:5]([I:28])=[C:6]([C:18]([I:27])=[C:19]([N:22]([CH3:26])[C:23](=[O:25])[CH3:24])[C:20]=1[I:21])[NH:7][C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20309648methyl 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)adipanilate

Product 1

HCID 203096393'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)adipanilic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 143.8 g. of methyl 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)adipanilate (Example 33) and 150 ml. of water was added dropwise 145 ml. of 10% sodium hydroxide solution. The reaction mixture was heated on a steam bath for two hours and then cooled and acidified with 3N hydrochloric acid solution. The solid product was collected and recrystallized from acetic acid to give 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)adipanilic acid in the form of a colorless solid, m.p. 267°-271° C. (dec.).

Workup

  1. additionTo a mixture of 143.8 g
  2. temperatureThe reaction mixture was heated on a steam bath for two hours
  3. temperaturecooled
  4. customThe solid product was collected
  5. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-a4f96740609147328106e42daa521f71
Source dataset
uspto-grants-1978_09
Patent number
US04111937

Reaction notes

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