4-Iodotoluene → N,N-diethyl-m-toluidine

HRID 1901293Notes

Reaction equation

HRID 1901293 reaction equation
[CH2:1]([N:3]([Sn](CCCC)(CCCC)CCCC)[CH2:4][CH3:5])[CH3:2].I[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:21]1[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][CH:20]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 122074-IodotolueneHCID 5315088Stannanamine, 1,1,1-tributyl-N,N-diethyl-

Product 1

HCID 66679N,N-diethyl-m-toluidine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Analogous reaction of N,N-diethylaminotributyltin with aromatic iodides were less efficient; however, satisfactory yields (>60% yields of isolated product) could be obtained in the presence of ammonium salts. Thus, the reaction of N,N-diethylaminotributyltin with p-iodotoluene in the presence of N-benzyltriethylammonium chloride in toluene at 100° C. afforded 3-(N,N-diethylamino)toluene in 63% isolated yield.

Sources & evidence

ORD record
ord-f56f90ffb4494f9186c60780878ae6ec
Source dataset
uspto-grants-1996_11
Patent number
US05576460

Reaction notes

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