Sodium Hydroxide → 5-Carbamoyl-3-hydroxymethyl-2,4,6-triiodobenzoic acid

HRID 1065065Notes

Reaction equation

HRID 1065065 reaction equation
[C:1]([C:3]1[C:4]([I:16])=[C:5]([CH2:14][OH:15])[C:6]([I:13])=[C:7]([C:11]=1[I:12])[C:8]([OH:10])=[O:9])#[N:2].[OH-:17].[Na+]>O>[C:1]([C:3]1[C:4]([I:16])=[C:5]([CH2:14][OH:15])[C:6]([I:13])=[C:7]([C:11]=1[I:12])[C:8]([OH:10])=[O:9])(=[O:17])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 129532475-Cyano-3-hydroxymethyl-2,4,6-triiodobenzoic acid

Product 1

HCID 198231115-Carbamoyl-3-hydroxymethyl-2,4,6-triiodobenzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

27.8 g of 5-cyano-3-hydroxymethyl-2,4,6-triiodobenzoic acid is suspended in 120 ml of water and dissolved by adding 10 g of sodium hydroxide. The batch is held at 60° C. for 3 hours and then precipitated into 50 ml of semiconcentrated sulfuric acid. After several hours of agitation in an ice bath, the precipitate is vacuum-filtered, washed with water, and dried at 50° C., thus obtaining 25 g of 5-carbamoyl-3-hydroxymethyl-2,4,6-triiodobenzoic acid as a white powder with a decomposition point above 280° C. Yield: 88% of theory.

Workup

  1. dissolutiondissolved
  2. customprecipitated into 50 ml of semiconcentrated sulfuric acid
  3. waitAfter several hours of agitation in an ice bath
  4. filtrationthe precipitate is vacuum-filtered
  5. washwashed with water
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-3f385ca4e0fd4d4aaaa1534662879ded
Source dataset
uspto-grants-1982_05
Patent number
US04328202

Reaction notes

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