Hydrogen iodide → 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621504Notes

Reaction equation

HRID 1621504 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[IH:28]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[I:28][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 2

HCID 24841Hydrogen iodideHCID 595482094-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 601556234-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineYield 65.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1020 mg, 2.65 mmol) and 67% hydriodic acid solution (0.499 mL, 6.63 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 19 h. The reaction mixture was diluted with NaHCO3 (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with saturated NaCl (20 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow solid. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 50% CH2Cl2/hexanes to give 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (826 mg, 1.734 mmol, 65.4% yield) as a mixture of product and starting material (3:1).

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as a light-yellow solid
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by silica gel chromatography
  10. washeluting with 50% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-47f1081e8c8449bc89abaec1fa5254ad
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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