Sulfuric Acid → HCID 20309659, compound

HRID 1763276Notes

Reaction equation

HRID 1763276 reaction equation
[NH2:1][C:2]1[C:3]([I:18])=[C:4]([C:8]([I:17])=[C:9]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[C:10]=1[I:11])[C:5]([OH:7])=[O:6].[C:19]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:20]1.S(=O)(=O)(O)O>O>[C:5]([C:4]1[C:3]([I:18])=[C:2]([C:10]([I:11])=[C:9]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[C:8]=1[I:17])[NH:1][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7940Glutaric anhydrideHCID 203096821949-42-4

Product 1

HCID 20309659HCID 20309659, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 58.6 g. of 3-amino-5-(N-methylacetamido)-2,4,6-triiodobenzoic acid, 74 g. of glutaric anhydride and 8 ml. of concentrated sulfuric acid was heated on a steam bath for 5 hours. The reaction mixture was poured into water and the solid product collected by filtration. The product, consisting of 3-glutarimido-5-(N-methylacetamido)-2,4,6-triiodobenzoic acid (Example 1) was dissolved in excess dilute aqueous sodium hydroxide, and the solution warmed for thirty minutes, then cooled and 3N hydrochloric acid added slowly until precipitation was complete. The solid product was collected and recrystallized first from acetone, then from acetic acid, and finally from water to give 3'-carboxy-5'-(N-methylacetamido)-2',4',6'-triiodoglutaranilic acid, colorless prisms, m.p. 188.8°-196.0° C.

Workup

  1. additionA mixture of 58.6 g
  2. filtrationthe solid product collected by filtration
  3. dissolutionwas dissolved in excess dilute aqueous sodium hydroxide
  4. temperaturethe solution warmed for thirty minutes
  5. temperaturecooled
  6. addition3N hydrochloric acid added slowly until precipitation
  7. customThe solid product was collected
  8. customrecrystallized first from acetone

Sources & evidence

ORD record
ord-1e70d7ca24324e55aab40c793997db4e
Source dataset
uspto-grants-1978_09
Patent number
US04111937

Reaction notes

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