Ammonia → HCID 21704254, compound

HRID 1106418Notes

Reaction equation

HRID 1106418 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][P:13]([OH:16])(=[O:15])[OH:14])[C:7](=[O:17])[C:6](=[O:18])[NH:5]2.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:28].[K+].N>O>[I:28][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][P:13]([OH:16])(=[O:15])[OH:14])[C:7](=[O:17])[C:6](=[O:18])[NH:5]2

Participants

7

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 21704250HCID 21704250, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21704254HCID 21704254, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

180 mg of 1-(6-amino-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)methanephosphonic acid is added dropwise to 10 ml of 25% strength sulfuric acid. After 5 minutes of agitation, a suspension of the salt is formed w which is cooled to 0° C. To this is added a solution of 60 mg of sodium nitrite in 2 ml of water. After 15 minutes of stirring at 0° C., the reaction mixture is almost dissolved. To this is added a solution of 180 mg of potassium iodide in 2 ml of water. The ice bath is removed and the mixture heated to 100° C. for 2 hours. The cooled-off reaction mixture is neutralized with concentrated ammonia solution and evaporated to dryness. The residue is extracted by boiling with ethanol and a small amount of water, filtered, and the filtrate is concentrated. After chromatography over silanized silica gel with water : methanol=4:1, 40 mg of 1-(6-Iodo-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)methanephosphonic acid is obtained, mp: 295-297° C.

Workup

  1. additiona suspension of the salt
  2. customis formed w which
  3. dissolutionthe reaction mixture is almost dissolved
  4. customThe ice bath is removed
  5. temperaturethe mixture heated to 100° C. for 2 hours
  6. customThe cooled-off reaction mixture
  7. customevaporated to dryness
  8. extractionThe residue is extracted
  9. filtrationa small amount of water, filtered
  10. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-b469e57e19e74b9c93b8535e78a2d4ad
Source dataset
uspto-grants-2000_05
Patent number
US06057304

Reaction notes

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