Ammonia → HCID 12940476, compound

HRID 1065060Notes

Reaction equation

HRID 1065060 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.N[C:11]1[C:12]([I:23])=[C:13]([C:17]([I:22])=[C:18](N)[C:19]=1[I:20])[C:14]([OH:16])=[O:15].[NH3:24].[Cu][C:26]#[N:27].[C-:28]#N.[K+].Cl>C(OCC)(=O)C.O.C(O)(=O)C>[C:28]([C:11]1[C:12]([I:23])=[C:13]([C:17]([I:22])=[C:18]([C:26]#[N:27])[C:19]=1[I:20])[C:14]([OH:16])=[O:15])#[N:24]

Participants

11

Reactant 7

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 216803,5-Diamino-2,4,6-triiodobenzoateHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 12940476HCID 12940476, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

7 g of sodium nitrite is introduced under stirring into 84 ml of concentrated sulfuric acid held at a temperature of +5° C. The mixture is then maintained at +70° C. until solution has occurred, and then cooled to +5° C. After adding 42 ml of glacial acetic acid dropwise under cooling, 21 g of 3,5-diamino-2,4,6-triiodobenzoic acid is added in incremental portions under agitation in such a way that the internal temperature ranges between 0° C. and +5° C. The batch is stirred for another 2 hours, and the green-colored suspension is poured on 400 g of ice. A mixture is prepared from 500 ml of concentrated ammonia and 320 ml water, and 35.6 g of copper(I) cyanide and 67 g of potassium cyanide are dissolved therein. To this solution, the diazotizing batch is added under strong frothing. The mixture is stirred for 2 hours, and after allowing the batch to stand overnight it is first combined with 500 ml of ethyl acetate, then with excess concentrated hydrochloric acid. After the thus-separated copper salts have been removed by vacuum-filtering and washed out with ethyl acetate, the aqueous phase in the filtrate is separated and extracted several times with ethyl acetate. The ethyl acetate extracts are combined, washed with water, and then dried over sodium sulfate and concentrated. The dark-colored residue is treated with 100 ml of acetone in the hot state; the acetonic solution is filtered off from undissolved components and thereafter concentrated to half the quantity. After stirring for several hours, the crystallized product is vacuum-filtered, washed with ice-cold acetone, and dried at 50° C., thus obtaining 8.5 g (=38% of theory) of 3,5-dicyano-2,4,6-triiodobenzoic acid as a white powder with a decomposition point lying above 280° C.

Workup

  1. customheld at a temperature of +5° C
  2. temperatureThe mixture is then maintained at +70° C. until solution
  3. temperaturecooled to +5° C
  4. temperatureunder cooling
  5. customranges between 0° C. and +5° C
  6. dissolutionare dissolved
  7. additionTo this solution, the diazotizing batch is added under strong frothing
  8. stirringThe mixture is stirred for 2 hours
  9. waitto stand overnight
  10. customAfter the thus-separated copper salts have been removed
  11. filtrationby vacuum-filtering
  12. washwashed out with ethyl acetate
  13. customthe aqueous phase in the filtrate is separated
  14. extractionextracted several times with ethyl acetate
  15. washwashed with water
  16. dry with materialdried over sodium sulfate
  17. concentrationconcentrated
  18. additionThe dark-colored residue is treated with 100 ml of acetone in the hot state
  19. filtrationthe acetonic solution is filtered off from undissolved components
  20. concentrationconcentrated to half the quantity
  21. stirringAfter stirring for several hours
  22. filtrationthe crystallized product is vacuum-filtered
  23. washwashed with ice-cold acetone
  24. customdried at 50° C.

Sources & evidence

ORD record
ord-5c537c755f24441893f12100f52dfd4b
Source dataset
uspto-grants-1982_05
Patent number
US04328202

Reaction notes

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