sS* ψ?Ρ* «m
DIMETHYL PHYSICAL P
P*OPERtlESva
«,%.-/"So»»
^«itanine solid • (5t · A appearance W l « t e , c r y s t a B . n N o n e ^ . odor
-""'-" h t"
.·
Λα8 13
·
Molecular * « # » · · · ' .
HYDANTOI
Λ '« o
178oC.
c
\
Fissure of t h e ring by heating with fuming hydrochloric acid solution at 150°-16O°C. or with sixty per cent sulphuric acid above 120°C. yields alpha-amino isobutyric acid. NH
ι .
l
«H'W , ethylace tate
Ι
oc
+ HC1 +· 2HaO — • HjC-C-C0OH + C0 2 +- N t ^ C l «H*
AH
Treatment with dilute sodium or b a r i u m h y d r o x i d e gives a salt of alpha-ureido isobutyric acid. 'CO
1 Solu^W-ater:
^
\
30 ' ;
| |
H^C
'
OC NH Substitution reactions on the Imino groups are illustrated by re action with boiling acetic anhydride which yields 1-acetyl dimethyl hydantoin. N-C0CH3 NH
L-^~H e r e is a n o t h e r v e r s a t i l e D u P o n t m a t e r i a l a v a i l a b l e for r e s e a r c h a n d d e v e l o p m e n t p u r p o s e s . V a r i o u s s u b s t i t u t i o n s c a n b e m a d e i n the imino a n d c a r b o n y l g r o u p s . F i s s u r e o f t h e ring is possible w i t h m i n e r a l acids a n d dilute alkali solutions. R e a c t i o n s w i t h formaldebiyde yield a v a r i e t y o f c o m p o u n d s , i n c l u d i n g m e t h y l o l derivatives, methylene-bis-(dimethyl h y d a n t o i n ) and. a series of resins v a r y i n g from v i s c o u s , oily l i q u i d s t o h a r d , brittle, t r a n s p a r e n t solids, all o f w h i c h a r e solixble i n w a t e r a n d m a y find a p p l i c a t i o n s a s sizing a g e n t s a n d textile assistants. M o n o - a n d d i N-chloro derivatives containing approximately 21.8% a n d 3 6 % b y w e i g h t o f active chlorine can b e p r e p a r e d b y c b l o r i n a t i o n . S o m e o f t h e reactions o f d i m e t h y l h y d a n t o i n are illustrated a t tfye right.
X
^ T HjC"
OC
.
V O L U M E
T H I N G · : · l-OR .THROUGH
2 4,
BETTER
OHSMiSTPY
*
CO
Ί |
H- C H 3 C 0 0 H
OC
NH
Hz
*V \ « JZ
\^ ^
JÇ
CO
H3C
I
SC
v / " NCO +
H5C
CH20
/
-NH
oc-
-NH
0C-
I
NH
H3CSXAJV>H ~co
.NH
H3C'
~CS
rS*
w
OC NH Reactions w i t h F o r m a l d e h y d e
Monomethylol—dimethyf
/
NH
JC'
N-_CH2
\ ~CO
OC
"κ~ Cy \ ^C
NH
OC
:
hydantoin
-N
C CO O
%/ ΝC"XCH3 OC OC
di
NH
HN
CO
Methylen e - bis—(df/nethyf
ΝΗ CO
OC-
EcTTER
— •
NH
H 3 c"
ιβρ.
(CH3CO)20
Replacement of the oxygen atoms by sulfur is effected by reac tion of dimethyl hydantoin with phosphorous trisuiflde i n tetralin as reaction medium, with the formation of 5,5-dimethyl-2r4-dithiohy,Λ NH ΝΗ dantoin.
AVAILABILITY—Limited quantities of this prod uct are available for. research and development. A request on ^our company letterhead will bring further technical information and also a sample if desired. B. I . du ¥>ont de Nemours & Co. (Inc.), Electro.
