Water → HCID 12303874, compound

HRID 1065066Notes

Reaction equation

HRID 1065066 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([I:20])=[C:7]([C:11]([I:19])=[C:12]([C:15](=[O:18])[NH:16][CH3:17])[C:13]=1[I:14])[C:8](N)=[O:9])=[O:4].N([O-])=[O:22].[Na+].O>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:1][NH:2][C:3]([C:5]1[C:6]([I:20])=[C:7]([C:11]([I:19])=[C:12]([C:15](=[O:18])[NH:16][CH3:17])[C:13]=1[I:14])[C:8]([OH:22])=[O:9])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 54119225HCID 54119225, compound

Product 1

HCID 12303874HCID 12303874, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

12.3 g of 3,5-bis(N-methylcarbamoyl)-2,4,6-triiodobenzoic acid amide is suspended in 80 ml of glacial acetic acid. Under agitation, a mixture of 1.66 g of sodium nitrite in 12 ml of concentrated sulfuric acid (prepared under ice cooling) is added in small portions at room temperature; during this step the temperature rises from 24° C. to 42° C. The mixture is then stirred for 3 hours at room temperature, 30 minutes at 50° C., and 90 minutes at 70° C. After agitating overnight at room temperature, the reaction mixture is stirred into 400 ml of water. The precipitate is vacuum-filtered after 4 hours, washed with water, and dried at 50° C. under vacuum. The crude product (11.9 g) is dissolved in 110 ml of water and 12 ml of 2 N sodium hydroxide solution, adjusted to pH 6.5 with 2 N acetic acid, and stirred for 30 minutes with 1 g of carbon. After the carbon has been removed by vacuum-filtering, the solution is precipitated with 16 ml of 2 N hydrochloric acid. After vacuum-filtering and drying at 50° C. under vacuum, 10.7 g (87% of theory) of 3,5-bis(N-methylcarbamoyl)-2,4,6-triiodobenzoic acid is obtained, mp>300° C.

Workup

  1. additionis added in small portions at room temperature
  2. customrises from 24° C. to 42° C
  3. custom90 minutes
  4. customat 70° C
  5. stirringAfter agitating overnight at room temperature
  6. filtrationThe precipitate is vacuum-filtered after 4 hours
  7. washwashed with water
  8. customdried at 50° C. under vacuum
  9. dissolutionThe crude product (11.9 g) is dissolved in 110 ml of water
  10. stirringstirred for 30 minutes with 1 g of carbon
  11. customAfter the carbon has been removed
  12. filtrationby vacuum-filtering
  13. customthe solution is precipitated with 16 ml of 2 N hydrochloric acid
  14. filtrationAfter vacuum-filtering
  15. customdrying at 50° C. under vacuum

Sources & evidence

ORD record
ord-0fc674a21ed64f6c99978d64ab2ab881
Source dataset
uspto-grants-1982_05
Patent number
US04328202

Reaction notes

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