SCIENTIFIC ABSTRACT LUGOVKIN, B.P. - LUGOVOY, V.N.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001030720008-0
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: April 3, 2001
• Sequence Number: 8
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

USSR/Chemistry Organophosphorus Compounds, Nov 52
"The Alkylation of Amines With Chloridea of Dialkyl-
phosphoric Acid," B. P. Lugovkin an dIB. A. Arbuzov,
Chem Inst imeni A. M. Butlerov, Kazan State U imeni
V. 1. Lenin
"Zhur Obshch Khim" Vol 22, No 11, pp 2o4l-2o47
The action of chlorides of diethylphosphoric acid
and dibutylphosphoric acid on carbazole was studied.
The heating of these Components above 2000 resulted
ifi-a, reaction which produced N-6thyl-* abd'N-butyl-
csibazolesl resp. The ilkylating action of the
chlorides of dialkylphosthoric acial --4is' also detd
on the examples of aniline, P-naphthylamine,
238T38
diphenylamice and x-aminopyridine'. Th react-Lon
resulted in N-diethylaniline(87%), N-diethyl-p-
na~ihthylamine(88%),'N-ethyldiphenylamine(83%),
N~-methyldiphenylamine(69%) and N-methylpyiidoni-
Zi&ne(29%),'resj;i-Alkylation with acid chlorides
of dialkylpho'sphoric acid was'shown to.take
,63Ac6 also-in the case of amides'of a6ids* 'To
explain the mechanism of the alkylati.n.9 action
of'the Acid chlorides, a study was"made'of'the
O-tf6ct of heat on the anilid6'O'f diethylphiDs-
Phoric acid. It was demonstrated that'-4hen the
latter 4is heated up to 2300 ylanili~e
d,eth,
(85%)'ims`,formed. A preliminary scheme'for the
fissibn-6f the anilide of diethylphosphoric acid
is givgn.
238T38

of the acid gave 7A C. 44Sr:kriV-# 62. 330.
-to 65-135* gave 72.770' la
3 FP(Cls heated 15 min. It, *v
*
,
O I h
h H
d
"
r.
t
w rA
I
: 0.9M (heate
bG jg2
c&
,d
O in sealed tube I hr. at
C &tia
J with 8 S
Ac
5
.
&
g.
g
-00' ove, after a length qa% A the arkydride
l
"
y "
ISG
~ beatZ I tm. with dil.-

h
47."* (froin dry R
of 1. M.
~!t
R
B.' A. Arbuzov and B. P.
TsrfFWc add Lugovkin
-
, ul,
ir'
- X
d
l:
(V
W
S "
NaOff readily gave 1), 1 g. " ydrida with 0.1 ff. Hr in
in. a3.5'. ~ I chloride (6.3
ave the fdrabromide
CHCI
v-
,
cntn State lunly.,
l
h
r
yan
Aaxan)i
.
Sldtef ObAchd Kkirs.j AW. Nauk S.S.S;R. 1, 419-24 ,
S g
~&!
added t,concd. NE40H with cooling gave 96.7% am e
-
'1109h d, Amaud, Comps, fftd 114 70(1692); 134,
om abs, MOH). which (6 g.) W*CJfCh
VEIL m - 88' Or
'
473(1002)."To 40.7 g, petroselinti: acid lit dry CHC!s wad^ treated with 4 g. Hr gave the di-Br aNiag of 1, fn. 80-90.6
slowly adifed 20 r. Br In 40 oil, CHC4 w1th Scod coolins;
'
f
h
b
in riun EtOll). It (L6.7 g.) and 8A ji. FA hca*cd it %bout
ng'1.4758. -
ba 15"'
~~
nitrile
60/
to 180 1
ave 16
n
-
a
ter evapa. d the solvent t
em was o
ed 77 g. 6,7-
m
1WOMM444 440, M. 87-84 (fumn E40) This 100 li.) In,
t .
1 g
,
,
ml
.
0
dU08790 Muxing 10S.M040g. ribs. Mc;OH withAg, -
157-90
be 104-V
b
2% 1 Ale ejlgr
02
11X~ 6 h;
150 ml. abs, StOH
an 4 rAftm bath, t
he
l
d 4
I and 20 S. rmid. KOH w2i; hea
ed a his,
hm treated with 24 c. powd. KOH mud
ft
411
l
h 5W
h
t
0 ,
,
.
m. gave
,
x4j 1AM0, d41% 0.8975, which with Or in CHCla gove the A' ."_
-T.S*(firosngtOH-OW). Simllarlywits
m.27
Orddriv
ugg.
Q"
ate
.
IleutrI1111411140111 wit, er
4- w
ani
9r; a
t
m
M
411, 1001 there was tamed 450% .
.,
ur*0. OILS% I FA Oster (111,k, bs 103-40, b, 202-41, mg
qrWe41Y q.Nr+C4rUQxY0C acid) (1). m, W a'
l980
rd
(((QM;1R(Ol0J
b
with3
iaCH
2WT 4&W df,* O.P.M6, dis 0,882A hydrolysis with 5% N&qH.:
1.5 hro. gave 1). pvc thet di rawide, 2 yellow 11 Wit, lig,l
g.
r
4
v
,
, 11 w
III in 6 uil
AC
5
heatin
1
d4 1
1320
4773
1
.
.
.
g.
.
.
g
;
,
10 -&S'
80*
di-Widd
in
th
l
70
l
-
. .
e
ire. at
,
e 2
gan
0.65 g. It
(from abs. EcOH), To 20.1 g. lit la 100 jid. dry Ru0H
'
,-
was adtW I C. No, after heming M-20 whi. to
the reacdoll, die Ulixt, Waa dild, with 11%0 (15 1111.), heate d
at 100,mWA hr., wasbcd w" flaO, wilted out with
d, Aelding; 0.7 S. inatetlal,'in. 20
~:aod theorg. layer eva N 1
41, ,
j
Crystsii -front AcOt changed this. tnatesial Complete
e
yielding wittic I und a,substarice, m.
mother liquorafW Wittion of thu tiroduct, m. P
4
% ru,
MANX, SCH04CIWIl, 1), 18:1
vv it di6rbm
th t!q v it di6rbm j*_
Ur in CflCh'
7
1
) witli
.
C.
C.
V
"k-3 G
M. fzj
ud u Wraboamidc
in
ll
li
id
.
.
an o
, a
,
qu
y

11777 7 77.

V,~; % 1LL