Toluene → HCID 22421319, compound

HRID 1441106Notes

Reaction equation

HRID 1441106 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.C[N-:11][CH3:12].[Li+].[C:14]1(C)C=CC=CC=1.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23]>C(OCC)C>[CH3:23][Si:22]([CH3:25])([CH3:24])[N:8]([CH3:14])[C:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1)=[N:11][CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 7724p-TolunitrileHCID 5152226Lithium N-methylmethanaminide

Product 1

HCID 22421319HCID 22421319, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

p-Tolunitrile (35.14 g, 0.30 mol) was contacted with lithium dimethylamide (15.31 g, 0.30 mol) in diethyl ether (250 mL) at room temperature. Replacement of the solvent by toluene, subsequent reaction with chlorotrimethylsilane (38.1 mL, 0.30 mol) and work-up of the reaction mixture afforded N-trimethylsilyl-N,N'-dimethyl-p-toluamidine in 52 percent yield. Fractional high vacuum distillation of this crude product (85° C., 2×10-3Torr) allowed the isolation of the pure product (36-37 g) as a low-melting (28° C.) colorless crystalline solid. The 1H NMR spectrum showed the aromatic protons of the tolyl group as an apparent doublet of doublets (δ7.08 ppm) due to an AA'BB' slitting pattern characteristic in para unsymmetrically disubstituted benzenes. The two methyl groups attached to the nitrogens were recorded as a broad singlet (~16 Hz) at 2.88 ppm.

Sources & evidence

ORD record
ord-fb897fa2adda4bce84a4e9622f156437
Source dataset
uspto-grants-1996_03
Patent number
US05502128

Reaction notes

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