Iodine → HCID 67513815, compound

HRID 1508522Notes

Reaction equation

HRID 1508522 reaction equation
N[C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=2[CH3:20])[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9].[I:21]I.CCCCCON=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:8]([C:7]1[CH:6]=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=2[CH3:20])=[CH:3][C:2]=1[I:21])[CH3:9]

Participants

6

Reactant 4

HCID 807IodineHCID 10026Pentyl nitriteHCID 24477Sodium ThiosulfateHCID 67513794HCID 67513794, compound

Product 1

HCID 67513815HCID 67513815, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3′-amino-4′-ethyl-2-methylbiphenyl-4-carboxylate (1.1263 g, 4.18 mmol) and iodine (0.258 ml, 5.02 mmol) were mixed in chloroform (40 mL) and immersed in a preheated oil bath (90° C. when immersed). To this hot mixture was added n-amyl nitrite (0.668 ml, 5.02 mmol). The reaction mixture was heated in an 80° C. oil bath for 2 hours then allowed to cool to ambient temperature overnight. The crude was stirred with a Na2S2O3 solution. Volatiles were removed under reduced pressure. The pot residue was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated. The resulting mixture was purified by flash chromatography (SiO2, Isolute Flash Si; 100 g). The column was eluted by an EtOAc/hexane mixture (0% to 30%). Related fractions were pooled and evaporated to afford a light yellow solid as the titled compound. LCMS calc.=380.03. found=381.09 (M+H)+.

Workup

  1. customimmersed in a preheated oil bath
  2. custom(90° C. when immersed)
  3. temperatureto cool to ambient temperature overnight
  4. customVolatiles were removed under reduced pressure
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting mixture was purified by flash chromatography (SiO2, Isolute Flash Si; 100 g)
  10. washThe column was eluted by an EtOAc/hexane mixture (0% to 30%)
  11. customevaporated

Sources & evidence

ORD record
ord-1382077a43024e8a9849bd4bfc368d08
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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