Methyl iodide → N~1~,N~3~-Diphenylpropane-1,3-diimine

HRID 865327Notes

Reaction equation

HRID 865327 reaction equation
C[C:2]1[C:10]([CH3:12])(C)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CC1S[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.IC>>[CH:21]1[CH:20]=[CH:19][C:17]([N:18]=[CH:12][CH2:10][CH:2]=[N:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:16][CH:22]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 84462-MethylbenzothiazoleHCID 154273H-Indole, 2,3,3-trimethyl-

Product 1

HCID 111090N~1~,N~3~-Diphenylpropane-1,3-diimine

Procedure

2,3,3-Trimethyl indolenine, methylbenzothiazole, iodomethane, and diidopropane were purchased from Aldrich and used without further purification. Malonaldehyde dianil was synthesized according to literature reports (Glauert, R. H. and Mann, F. G. J. Chem. Soc. (1952) 5012, by the method of Claisen Ber. (1903) 36, 3668). Dry nitrobenzene was freshly distilled from CaH2. Dry triethylamine was distilled from Na°. DMF was predried with MgSO4, fractionally distilled and stored over molecular sieves. All dry solvents were stored under N2. All reactions were run under anhydrous conditions under N2. Reactions were monitored by TLC (silica gel 60, A260, Fisher) and visualized with short and long wavelength UV irradiation. Flash column chromatography was performed on silica gel 60 (200-440 mesh Fluka).

Workup

  1. customused without further purification
  2. distillationDry nitrobenzene was freshly distilled from CaH2
  3. distillationDry triethylamine was distilled from Na°
  4. distillationfractionally distilled
  5. customlong wavelength UV irradiation

Sources & evidence

ORD record
ord-518cc7e563464e1c9671a56f2b270d0c
Source dataset
uspto-grants-1996_10
Patent number
US05565554

Reaction notes

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