Potassium Iodide → HCID 59621121, compound

HRID 2061325Notes

Reaction equation

HRID 2061325 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:3]=1.N([O-])=O.[Na+].[I-:22].[K+]>O.Cl>[I:22][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 59621123HCID 59621123, compound

Product 1

HCID 59621121HCID 59621121, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
-2.5 °C

Procedure

To a cooled (0 to −5° C.), stirred suspension of 4-amino-2-(4-methoxy-benzyl)-1-methyl-benzene (18.3 g) in water (70 mL) and concentrated hydrochloric acid (20 mL) is added a solution of sodium nitrite (5.8 g) in water (20 mL). The suspension is stirred until homogenous and then a solution of potassium iodide (14 g) in water (20 mL) is added. The cooling bath is removed and the solution is stirred at 40° C. for 1 h and at 70° C. for another 1.5 h. After cooling to ambient temperature, aqueous sodium thiosulfate solution is added and the resulting solution is extracted with ethyl acetate. The combined extracts are dried (sodium sulphate) and the solvent is evaporated. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 19.1).

Workup

  1. additionis added
  2. customThe cooling bath is removed
  3. stirringthe solution is stirred at 40° C. for 1 h and at 70° C. for another 1.5 h
  4. temperatureAfter cooling to ambient temperature
  5. additionaqueous sodium thiosulfate solution is added
  6. extractionthe resulting solution is extracted with ethyl acetate
  7. dry with materialThe combined extracts are dried (sodium sulphate)
  8. customthe solvent is evaporated
  9. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 19.1)

Sources & evidence

ORD record
ord-c5e3e2b2b724456283e8fc4d4321b206
Source dataset
uspto-grants-2012_10
Patent number
US08283326B2

Reaction notes

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