Hydrochloric Acid → HCID 20309621, compound

HRID 437377Notes

Reaction equation

HRID 437377 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 ten minutes, 18 ml. more of 10% sodium hydroxide was added, and the mixture heated one 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 ten minutes
  4. temperaturethe mixture heated one 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-d97a02232ee64ca59752045cebcd5e05
Source dataset
uspto-grants-1977_06
Patent number
US04031088

Reaction notes

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