Hydrochloric Acid → HCID 136133301, compound

HRID 505832Notes

Reaction equation

HRID 505832 reaction equation
B(O)(O)O.Cl.[I:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH3:14])[CH:8]=1.[N:15]([O-])=O.[Na+].[CH:19]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([CH3:26])[CH:20]=1.[OH-].[Na+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>O>[I:6][C:7]1[CH:13]=[CH:12][C:10]([N:11]=[N:15][C:19]2[CH:20]=[C:21]([CH3:26])[CH:22]=[CH:23][C:24]=2[OH:25])=[C:9]([CH3:14])[CH:8]=1

Participants

9

Reactant 7

HCID 313Hydrochloric Acid3×HCID 2879P-CresolHCID 7628Boric AcidHCID 14798Sodium Hydroxide2×HCID 24243Trisodium PhosphateHCID 832214-Iodo-o-toluidine2×HCID 23668193Sodium Nitrite3×

Product 1

HCID 136133301HCID 136133301, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask is charged with 100 mmol of boric acid followed by 6N HCl solution to adjust the reaction solution to a pH of 2. Once the salt dissolves, 20 mmol of 4-iodo-2-methylaniline is added to the reaction solution, followed by enough ice to reduce solution temperature to 0° C. In a separate flask, 20 mmol of sodium nitrite (NaNO2) is dissolved in ice water. The NaNO2 solution is added drop-wise with constant stirring to the 4-iodo-2-methylaniline solution. The pH of the reaction solution is maintained by addition of 6N HCl. After the NaNO2 solution addition is complete, ice is added to maintain the 0° C. reaction temperature. A 3rd flask is charged with 20 mmol of p-cresol, water and 2.5 N NaOH (20 mmol), which is then added drop wise to the ice cooled reaction with constant stirring. The reaction mixture is allowed to stir for 15 min at pH 2.0-2.5. NaOH (2.5 N) is then added in small aliquots to the reaction solution to increase the pH to 8.5. The reaction solution is allowed to warm to room temperature. Dibasic sodium phosphate solution (100 mmol) is added and the pH is adjusted to 6.0 with 6 N HCl. The product is filtered, rinsed with ice water and air dried. The product is purified by column chromatography to yield 2-(4-iodo-2-methyl-phenylazo)-4-methyl-phenol (3).

Workup

  1. dissolutionOnce the salt dissolves
  2. customto 0° C
  3. additionice is added
  4. temperatureto maintain
  5. customthe 0° C. reaction temperature
  6. temperaturecooled
  7. customreaction with constant stirring
  8. temperatureto increase the pH to 8.5
  9. filtrationThe product is filtered
  10. washrinsed with ice water and air
  11. customdried
  12. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-8b2b25c14ac045478b2e0715935407f8
Source dataset
uspto-grants-2010_08
Patent number
US07781571B2

Reaction notes

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