Hydrochloric Acid → HCID 54500418, compound

HRID 2412974Notes

Reaction equation

HRID 2412974 reaction equation
N[C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.Cl.[N+]([O-])([O-])=O.[Na+].[I-:30].[K+]>C(OCC)(=O)C.O>[I:30][C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 24268Sodium NitrateHCID 13370669HCID 13370669, compound

Product 1

HCID 54500418HCID 54500418, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 53.9 g. of 4'-amino-4,4"-dimethoxy-1,1':2',1"-terphenyl in 79 ml. of hydrochloric acid and 120 ml. of water was cooled by means of an external ice bath to about 0° C. A solution of 13.11 g. of sodium nitrate in 100 ml. of water was added over a ten minute period. After stirring an additional ten minutes, a solution of 29.9 g. of potassium iodide in 100 ml. of water was added over a 30 minute period. The solution was allowed to stand overnight without stirring. The reaction was then heated on a steam bath for 30 minutes. After cooling, two liters of ethyl acetate were added. The layers were separated and the aqueous layer was extracted four times each with 500 ml. of ethyl acetate. The combined organic extracts were washed four times each with 250 ml. of a 10% aqueous sodium thiosulfate solution, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography over silica gel to provide 35.12 g. of the desired iodo intermediate.

Workup

  1. stirringwithout stirring
  2. temperatureThe reaction was then heated on a steam bath for 30 minutes
  3. temperatureAfter cooling
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted four times each with 500 ml
  6. washThe combined organic extracts were washed four times each with 250 ml
  7. dry with materialof a 10% aqueous sodium thiosulfate solution, dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography over silica gel
  11. customto provide 35.12 g

Sources & evidence

ORD record
ord-50b0bea0f04a49559fa1a548f15ac926
Source dataset
uspto-grants-1985_01
Patent number
US04495202

Reaction notes

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