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

HRID 962886Notes

Reaction equation

HRID 962886 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, 3664). 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.

Workup

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

Sources & evidence

ORD record
ord-2d8dda8314e14012bd68143b2834bfc2
Source dataset
uspto-grants-1998_06
Patent number
US05760201

Reaction notes

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