Synthesis of N-[chloro(diorganyl)silyl]anilines

Article abstract of DOI:10.1134/S107036321405017X

A series of N-[chloro(diorganyl)silyl]anilines RR′Si(NR'Ph)Cl (R, R′ = Me, Ph, CH₂=CH, ClCH₂, Cl(CH₂) ₃; R' = H, Me) was prepared via the reaction of diorganyldichlorosilanes with aniline or N-ethylaniline in the presence of triethylamine.

Full text of DOI:10.1134/S107036321405017X

ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 5, pp. 883–887. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.Yu. Nikonov, I.V. Sterkhova, N.F. Lazareva, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 789–793.
Synthesis of N-[Chloro(diorganyl)silyl]anilines
A. Yu. Nikonov, I. V. Sterkhova, and N. F. Lazareva
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
е-mail: nataly_lazareva@irioch.irk.ru
Received August 26, 2013
Abstract—A series of N-[chloro(diorganyl)silyl]anilines RR'Si(NR''Ph)Cl (R, R' = Me, Ph, CH2=CH, ClCH2,
Cl(CH2)3; R'' = H, Me) was prepared via the reaction of diorganyldichlorosilanes with aniline or N-ethylaniline
in the presence of triethylamine.
Keywords: N-silylamine, N-[Chloro(diorganyl)silyl]aniline, aniline, silane
DOI: 10.1134/S107036321405017X
Chemistry of N-silylated amines has been inten-
sively developing over the last fifty years [1–6]. The
interest to these compounds is due to their unique
physico-chemical properties: the organosilicon
substituent adjacent to the nitrogen atom causes
structural changes of the amino group [7–11] and
decreases the nitrogen atom basicity [12–14]. These
compounds are widely used as synthons [15–20] and
silylating agents [21–24] in synthetic organic and
organoelement chemistry. N-Silylamines are promising
volatile precursors for chemical vapor deposition of
silicon nitride and oxynitride as well as for preparation
of new materials, including metallated nanomaterials
and membranes [25–30]. To date, several thousands of
monosilylated amines have been synthesized, and their
structure and chemical properties have been
characterized. Extending our studies of reactivity of α-
silylamines [31, 32] we aimed to investigate chemical
properties of the following type of compounds:
RR'NCH2Si[N(Ar)R'']nX3–n (R, R', R'' = Alk, Ar; X =
Alk, Ar, OAlk, OAr; n = 1–3). So far, they have been
scarcely studied: to the best of our knowledge there are
only a few publications on their synthesis and
properties [33–36]. Amination of halogenomethyl-
silanes with amines is known as the most convenient
synthetic route to α-silylamines RR'NCH2SiX3 [37,
38]. Therefore, the target compounds to be studied in
this work could be prepared via reaction of the
corresponding (halogenomethyl)(N-arylamino)silanes
HalCH2Si(NarR'')nX3–n with amines. However, only a
few (halogenomethyl)(N-arylamino)silanes have been
described in the literature: bromo- and chloromethyl
(dimethyl)anilinosilanes PhNHSiMe2CH2Hal [35, 39–
41], chloromethyl(dimethyl)(N-methylanilino)silane
PhN(Me)SiMe2CH2Cl [42], o- and p-chloromethyl(di-
methyl)(N-trimethylsiloxyanilino)silane Me3SiOC6H4NH·
SiMe2CH2Cl [43], whereas information on synthesis of
polyfunctional amino(chloro)silanes HalCH2SiR
(NArR')Hal has been missing. Noteworthily, even the
simplest mixed diorganyl(chloro)aminosilanes RR'Si
(NR2)Cl has been almost not studied. Therefore, the
goal of this work has transformed into elaborating the
method to prepare N-[chloro(diorganyl)silyl]anilines
RR'Si(NR''Ph)Cl (R, R' = Me, Ph, CH2=CH, ClCH2,
Cl(CH2)3; R'' = H, Me), new promising synthons for
organic synthesis and material chemistry. The only
compound of this series described in the literature is
(anilino)dimethylchlorosilane [44].
The synthesis conditions were optimized using the
reaction of dimethylchlorosilane with N-methylaniline
as an example, effects of the solvent, the base,
temperature and the ratio of the reagents on the yield
of the reaction product I was investigated (Table 1).
Me2SiCl2 + PhNHMe → PhMeNSiMe2Cl.
I
The reaction was performed by slow addition of the
solution of the mixture of N-methylaniline and
acceptor of HCl (triethylamine, pyridine, or excess of
N-methylaniline) to the solution of the silane, not
allowing the temperature to rise above 25°С, followed
by heating (if needed) to the desired reaction
883

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NIKONOV et al.
Effect of solvent, base, ratio of reagents, and temperature on the yield of compound I
Ratio of reagents
(silane : aniline : base)
Solvent
Et2O
Base
Et3N
Temperature, оС
Time, h
Yield, %
r.t.
r.t.
r.t.
34
r.t.
66
r.t.
68
r.t.
50
50
80
80
50
50
r.t.
80
60
110
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 1.1
1 : 1 : 2
48
48
96
12
48
12
48
10
48
24
24
10
24
24
24
48
48
24
10
56
32а
62
42
52
49
58
59
72
76
40а
73
76
75
77
19
44
80
75
Et2O
Et3N
Et2O
Et3N
Et2O
Et3N
THF
Et3N
THF
Et3N
Hexane
Hexane
Benzene
Benzene
Benzene
Benzene
Benzene
Benzene
Benzene
Benzene
Benzene
Toluene
Toluene
Et3N
Et3N
Et3N
Et3N
Et3N
Et3N
Et3N
pyridine
Et3N
PhMeNH
PhMeNH
Et3N
1 : 2
1 : 2
1 : 1 : 1.1
1 : 1 : 1.1
Et3N
a The reaction was performed by dropwise addition of the silane to the mixture of amines.
temperature after the reagents we fully mixed. As
follows from Table 1, the highest yield of compound I
was observed when using benzene or toluene as a
solvent. The optimal time of heating depends on the
temperature (in particular, 10 h at reflux and 24 h at
50°С). Further increase of the reaction time did not
improve the target product yield, but led to formation
of small amount of bis(N-methylanilino)dimethyl-
silane. Reverse order of the reagents mixing resulted in
substantial decrease of the of the target product yield
accompanied by formation of large amount (up to
35%) of bis(N-methylanilino)dimethylsilane, a side
product of the reaction. Using pyridine instead of
triethylamine or introduction of large excess of
triethylamine had no noticeable effect on the yield of
the product.
N-[Chloro(diorganyl)silyl]anilines RR'Si[N(R'')Ar]
Cl (II–XI) were synthesized via the reaction of the
corresponding diorganyldichlorosilanes with aniline or
N-methylaniline in the presence of triethylamine as
scavenger of HCl in benzene or toluene as solvent.
R1R2SiCl2 + PhNHR3 → PhR3NSiR1R2Cl,
R1 = Me, R2 = Ph, R3 = H (II); R1 = Me, R2 = Ph, R3 = Me
(III); R1 = Me, R2 = Vinyl, R3 = H (IV); R1 = Me, R2 =
Vinyl, R3 = Me (V); R1 = R2 = Ph, R3 = H (VI); R1 = R2 =
Ph, R3 = Me (VII); R1 = Me, R2 = ClCH2, R3 = H (VIII);
R1 = Me, R2 = ClCH2, R3 = Me (IX); R1 = Me, R2 = Cl(CH2)3,
R3 = H (X); R1 = Me, R2 = Cl(CH2)3, R3 = Me (XI).
The obtained compounds were viscous, sometimes
slowly crystallizing yellowish liquids with specific
odor. The refractive index was determined only for a
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SYNTHESIS OF N-[CHLORO(DIORGANYL)SILYL]ANILINES
few selected compounds, as high viscosity and
susceptibility to hydrolysis did not allow for reliable
results. Noteworthily, the reaction of diorganyldi-
chlorosilanes with N-methylaniline proceeded more
smoothly than in the case of aniline, leading to forma-
tion of the corresponding N-[chloro(diorganyl)silyl]-N-
methylanilines in satisfactory yields (53–80%). As side
products, in some cases small amounts (3–5%) of
diorganyl-bis(N-methylanilino)silanes RR'Si(NMePh)2
could be isolated. The yield of N-[chloro(diorganyl)
silyl]anilines was much lower (15–64%). Apparently,
that was mainly due to side reactions between the NH-
and SiCl-containing species at high temperature upon
distillation. The residue after distillation of the reaction
mixture appeared as resin and contained a number of
non-identified Si-containing products. The 29Si NMR
spectra of the distillation residue normally contained
five to ten signals of varied intensity. Unfortunately,
all trials purify N-[chloro(diorganyl)silyl]anilines by
means of column chromatography failed. Structure of
the prepared compounds was confirmed by multi-
nuclear NMR experiments (1H, 13C, and 29Si).
When the aniline addition was complete, the reaction
mixture was heated to 50–60°С with stirring on the water
bath during 4–5 days. The formed precipitate was filtered
off and carefully washed with the same solvent. The
solvent was removed from the filtrate with rotary
evaporator, the residue was distilled in vacuum.
N-[Chloro(dimethyl)silyl]-N-methylaniline (I).
Yield 80%, bp 68°С (2–3 mmHg), nD20 1.5212. H NMR
1
spectrum, δ, ppm: 0.1 s (6H, CH3Si), 2.96 s (3H, CH3N),
13
7.23–7.46 m (5H, PhN). C NMR spectrum, δ, ppm:
1.78 (CH3Si), 26.7 (CH3N), 122.5 (Co), 129.3 (Cp), 130.2
(Cm), 137 (Ci). 29Si NMR spectrum, δ, ppm: 7.38.
Found, %: C 54.36; H 7.41; N 5.12. C9H14ClNSi.
Calculated, %: C 54.12; H 7.06; N 7.01.
N-[Chloro(phenylmethyl)silyl]aniline (II). Yield
20%, bp 150°С (2 mmHg). 1H NMR spectrum, δ, ppm:
0.8 s (3H, CH3), 4.06 br.s (1H, NH), 6.7–7.1 m (5H,
PhN), 7.4–7.7 m (5H, PhSi). 13C NMR spectrum, δC,
ppm: 1.8 (CH3Si), 117.3 (Cp, PhN), 120.6 (Co, PhN),
128.3 (Cm, PhN), 129 (Cm, PhSi), 130.8 (Cp, PhSi), 132.9
29
(Ci, PhSi), 133.7 (Co, PhSi), 144.1 (Ci, PhN). Si NMR
spectrum, δ, ppm: 7.46. Found, %: C 62.74; H 5.28; N
5.43. C13H14ClNSi. Calculated, %: C 63.01; H 5.69; N
5.65.
The prepared polyfunctional silanes are of high
synthetic potential. In particular, we believe that the
presence of labile Si–Cl bond will allow using them as
synthons to prepare N-([diorganyl]hydroxysilyl)anilines,
N-([diorganyl]alkoxysilyl)anilines, and N-([diorganyl]-
aminosilyl)anilines as well as nitrogen- and silicon-
containing heterocycles.
N-[Chloro(phenylmethyl)silyl]-N-methylaniline
1
(III). Yield: 55%, bp 116°С (2 mmHg). H NMR
spectrum, δ, ppm: 0.67 s (3H, CH3Si), 2.9 s (3H, CH3N),
13
6.9–7.2 m (5H, PhN), 7.3–7.6 m (5H, PhSi). C NMR
spectrum, δ, ppm: 2.6 (CH3Si), 37 (CH3N), 112.4 (Co,
PhN), 122.2 (Cp, PhN), 128 (Cm, PhSi), 128.7 (Cm, PhN),
130.6 (Cp, PhSi), 132.9 (Ci, PhSi), 133.9 (Co, PhSi),
148.6 (Ci, PhN). 29Si NMR spectrum, δ, ppm: –3.7.
Found, %: C 64.53; H 6.17; N 5.29. C14H16ClNSi.
Calculated, %: C 64.22; H 6.16; N 5.35.
EXPERIMENTAL
NMR spectra of the synthesized compounds were
registered in CDCl3 solution with the Bruker DPX-400
instrument (1H, 400.1 MHz; 13C 100.6 MHz; 29Si,
79.5 MHz) with HMDS or cyclohexane as internal
reference. All reactions were performed using the
thoroughly dried solvents purified by the known proce-
dures [45]. Triethylamine, anilines, and silanes were
distilled before use.
N-[Chloro(methyl)(vinyl)silyl]aniline (IV). Yield
1
15.4%, bp 78–82°С (2 mmHg). H NMR spectrum, δ,
ppm: 0.65 s (3H, CH3), 3.9 br.s (1H, NH), 6.16 t (1H,
HC-Si), 6.6–6.7 d.d (2H, CH2=), 6.8–7.2 m (5H, PhN).
13C NMR spectrum, δC, ppm: 0.6 (CH3Si), 117 (Cp),
119.5 (Co), 129 (Cm), 133.3 (HC-Si), 136.6 (CH2=), 143.9
Synthesis of compounds I–XI (general procedure).
Three-necked flask equipped with a thermometer,
dropping funnel and condenser was placed at water bath
and charged with the solvent and the silane (150 mL of
benzene or toluene per 0.1 mol of silane). Mixture of the
corresponding aniline or N-methylaniline with triethyl-
amine in the same solvent (100 mL of the solvent per
0.1 mol of silane) was slowly added dropwise to the flask
upon vigorous stirring, not allowing the temperature to
rise above 20–25°С. The molar ratio amine:silane was of
1 : 1, and 15–20% excess of triethylamine was used.
29
(Ci). Si NMR spectrum, δSi, ppm: 8.7. Found, %: C
54.46; H 6.51; N 6.96. C9H12ClNSi. Calculated, %: C
54.67; H 6.12; N 7.08.
N-[Chloro(methyl)(vinyl)silyl]-N-methylaniline
(V). Yield 72%, bp 63°С (2 mmHg). 1H NMR spectrum,
δ, ppm: 0.57 s (3H, CH3Si), 3 s (3H, CH3N), 5.9–6.2 m
(3H, H2C=CH), 7–7.2 m (5H, PhN). 13C NMR spectrum,
δC, ppm: 1.8 (CH3Si), 36.7 (CH3N), 118.2 (Cp), 122.1
(Co), 128.9 (Cm), 134.2 (HC-Si), 136.2 (CH2=), 148.9
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NIKONOV et al.
(Ci). Found, %: C 56.43; H 6.71; N 6.59. C10H14ClNSi.
Calculated, %: C 56.72; H 6.66; N 6.61.
N-[Chloro(3-chloropropyl)(methyl)silyl]-N-
methylaniline (XI). Yield 53%, bp°С (1 mmHg). H
1
NMR spectrum, δ, ppm: 0.5 s (3H, CH3Si), 1.1 m (2H,
CH2Si), 1.8 m (2H, –CH2–), 3 s (3H, CH3N), 3.4 m (2H,
CH2Cl), 7.0–7.2 m (5H, Ph). 13C NMR spectrum, δC,
ppm: 2 (CH3Si), 15.8 (CH2Si), 26.5 (–CH2–), 26.9
(CH3N), 47 (CH2Cl), 112.4 (Cp), 123.0 (Co), 129.0 (Cm),
149.0 (Ci). Si NMR spectrum, δ, ppm: -14.4. Found,
%: C 49.92; H 6.08; N 5.09. C11H17Cl2NSi. Calculated,
%: C 50.38; H 6.53; N 5.34.
N-[Chloro(diphenyl)silyl]aniline (VI). Yield: 64%,
bp 170–188°С (2 mmHg), mp 80.7°C. H NMR spec-
1
trum, δ, ppm: 4.1 s (1H, NH), 6.7–7.0 m (5H, PhN), 7.3–
7.7 m (10H, PhSi). 13C NMR spectrum, δC, ppm: 117.5
(Co, PhN), 119.5 (Cp, PhN), 128.1 (Cm, PhSi), 128.9 (Cm,
PhN), 130.9 (Cp, PhSi), 132.1 (Ci, PhSi), 134.4 (Co,
29
29
PhSi), 144 (Ci, PhN). Si NMR spectrum, δ, ppm: 0.7.
Found, %: C 70.05; H 5.37; N 4.37. C18H16ClNSi.
Calculated, %: C 69.77; H 5.20; N 4.52.
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