Hydrochloric Acid → HCID 20309621, compound

HRID 1763285Notes

Reaction equation

HRID 1763285 reaction equation
[C:1]([C:4]1[C:5]([I:31])=[C:6]([C:21]([I:30])=[C:22]([N:25]([CH3:29])[C:26](=[O:28])[CH3:27])[C:23]=1[I:24])[NH:7][C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])([OH:3])=[O:2].[OH-].[Na+].Cl>O>[C:1]([C:4]1[C:5]([I:31])=[C:6]([C:21]([I:30])=[C:22]([N:25]([CH3:29])[C:26](=[O:28])[CH3:27])[C:23]=1[I:24])[NH:7][C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 20309618HCID 20309618, compound

Product 1

HCID 20309621HCID 20309621, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 136.5 g. of methyl 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)azelanilate and 180 ml. of water was treated with 10% aqueous sodium hydroxide (about 140 ml.), added dropwise until solution was complete. The mixture was heated on a steam bath for 10 minutes, 18 ml. more of 10% sodium hydroxide was added, and the mixture heated 1 hour longer. The reaction mixture was cooled, acidified with 3% hydrochloric acid, and the solid product collected, washed with water, dried and recrystallized from acetic acid to give 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)azelanilic acid as a colorless solid, m.p. 205°-208° C.

Workup

  1. additionA mixture of 136.5 g
  2. additionadded dropwise until solution
  3. temperatureThe mixture was heated on a steam bath for 10 minutes
  4. temperaturethe mixture heated 1 hour longer
  5. temperatureThe reaction mixture was cooled
  6. customthe solid product collected
  7. washwashed with water
  8. customdried
  9. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-96b4107c564e441bbe235b86cd4324db
Source dataset
uspto-grants-1978_09
Patent number
US04111937

Reaction notes

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