A facile synthesis of aminoiminomethanesulfonic acid

Article abstract of DOI:10.1081/SCC-100105659

Aminoiminomethanesulfonic acid was conveniently obtained by oxidation of aminoiminomethanesulfinic acid with H₂O₂ in a high yield and good purity.

Full text of DOI:10.1081/SCC-100105659

This article was downloaded by: [Illinois State University Milner Library]
On: 19 November 2012, At: 00:11
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer
House, 37-41 Mortimer Street, London W1T 3JH, UK
Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic
Chemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
A FACILE SYNTHESIS OF AMINO-
IMINOMETHANESULFONIC ACID
Fenggang Pan a & Zhixin Pan b
a School of Chemical Engineering, Tianjin University, Tianjin, 300 072, China
b Department of Chemistry, Yantai Teachers' University, Yantai, 264 000, China
Version of record first published: 16 Aug 2006.
To cite this article: Fenggang Pan & Zhixin Pan (2001): A FACILE SYNTHESIS OF AMINO-IMINOMETHANESULFONIC ACID,
Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 31:19,
2891-2893
To link to this article: http://dx.doi.org/10.1081/SCC-100105659
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to
anyone is expressly forbidden.
The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses
should be independently verified with primary sources. The publisher shall not be liable for any loss, actions,
claims, proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.

SYNTHETIC COMMUNICATIONS, 31(19), 2891–2893 (2001)
A FACILE SYNTHESIS OF AMINO-
IMINOMETHANESULFONIC ACID
Fenggang Pan1, and Zhixin Pan2
*
1School of Chemical Engineering,
Tianjin University, Tianjin, 300 072, China
2Department of Chemistry, Yantai Teachers’
University, Yantai, 264 000, China
ABSTRACT
Aminoiminomethanesulfonic acid was conveniently obtained
by oxidation of aminoiminomethanesulfinic acid with H2O2 in
a high yield and good purity.
Aminoiminomethanesulfonic acid (AIMSOA) is an important agent
for synthesis of guanyl and guanido derivatives.1–6 It is readily attacked by
nucleophiles. Its preparation has been reported by Miller1 and Kim.2
Peracetic acid was employed as oxidant by both of them. When we repeated
their procedures, unfortunately we failed to achieve the reported yield. We
therefore attempted to find a cheap, simple and reliable procedure for pre-
paration of AIMSOA. Under optimized conditions, we employed amino-
iminomethanesulfinic acid (AIMSA) as the starting material as Keekyung
Kim2 did, with H2O2 as oxidant in aqueous medium.
*Corresponding author.
2891
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

ORDER
REPRINTS
2892
PAN AND PAN
AIMSOA was obtained in 93% yield and 98.5% purity. AIMSOAꢀH2O
was first reported and studied by us. The reaction takes place as illustrated
below.
The starting material (AIMSA) is a cheap and commercially available
reagent. The method reportedhere has several advantageous over the reported
procedures.1,2 Further, AIMSOAꢀH2O has not been reported previously. We
have studied its properties and optimized the conditions for its preparation.
AIMSOAꢀH2O was analysed by differential thermal analysis (DTA)
and thermo-gravimetric analysis. Dehydration occurs at 42ꢁC. The thermo-
gravimetric analytical results determined the amount of water to be 12.3%,
while the calculated value of AIMSOAꢀH2O was 12.68%.
The reaction parameters were optimized as reported here for increas-
ing the yield of AIMSOA. Above 70ꢁC the reaction was fierce and out of
control, while the reaction proceed smoothly at 50ꢁC. Given the probability
of side-reactions caused by concentrated H2SO4, we employed 0.5 N H2SO4
to catalyse the reaction. The theoretical amount of H2O2 was sufficient and
the optical reaction time was 70 min.
The proposed processes are therefore expected to be advantageous
procedures for the economical manufacture of AIMSOA. We have
successfully prepared amino guanidine and guanyl glycine with the obtained
AIMSOA.
EXPERIMENTAL
IR spectra were recorded on a Shimadzu IR-440 infrared spectro-
photometer as KBr discs. Elemental analyses were performed on a
Carlo-Erba 1106 elemental analyser. Differential thermal analyses were
carried out with a CRT-1 differential thermal analyser made in Shanghai.
Preparation of AIMSOA
In a two-necked round bottom flask (100 mL) equipped with a mag-
netic stirrer, 21.6 g AIMSA was added H2O2 (0.2 mol) in 23 mL 0.5 N H2SO4

ORDER
REPRINTS
AIMSOA
2893
aqueous solution by dropwise at 50ꢁC. After stirring at the same tempera-
ture for 70 min. The mixture was cooled by ice–water and filtered to afford
white glittering crystals. The crystals were washed twice by ice–water and
crystallized from water and dried at less than 30ꢁC. The obtained
AIMSOAꢀH2O was heated at 60ꢁC for 5 h and AIMSOA was prepared in
93% yield and 98.5% purity.
AIMSOA ꢀ H2O: IR ðKBrÞ n: 3420, 3245, 1700, 1220, 1050 cmꢂ1
.
Anal. calcd. for CH6O4N2S: C, 8.45; H, 4.23; N, 19.7; S, 22.5; Found: C:
8.74; H: 4.17; N: 19.8; S: 22.7.
AIMSOA: IR (KBr) n: 3430, 3240, 1710, 1220, 1050 cmꢂ1 Anal. calcd.
for CH4O3N2S: C, 9.68; H, 3.22; N, 22.58; S, 25.81; Found: C: 9.7; H: 3.1;
N: 22.3; S: 25.7.
REFERENCES
1. Miller, A.E.; Bischoff, J.J. Synthesis 1986, 777.
2. Kim, K.; Lin, Y.T.; Mosher, H.S. Tetrahedron Lett. 1988, 3183.
3. Kimball, S.D.; Das, J.; Lau, W.F. Eur. Patent 601 1994, 459.
4. Ackerman, J.; Banner, D.; Gubernator, K. Eur. Patent 468 1992, 231.
5. Lanyu, M.; Changmao, H. Chin. Patent 1 1994, 084, 505.
6. Crombic, L.; Jarrett, S.R.M. J. Chem. Soc. Perkin Trans. 1992, 3179.
Received in the UK May 31, 2000

Request Permission or Order Reprints Instantly!
Interested in copying and sharing this article? In most cases, U.S. Copyright
Law requires that you get permission from the article’s rightsholder before
using copyrighted content.
All information and materials found in this article, including but not limited
to text, trademarks, patents, logos, graphics and images (the "Materials"), are
the copyrighted works and other forms of intellectual property of Marcel
Dekker, Inc., or its licensors. All rights not expressly granted are reserved.
Get permission to lawfully reproduce and distribute the Materials or order
reprints quickly and painlessly. Simply click on the "Request
Permission/Reprints Here" link below and follow the instructions. Visit the
U.S. Copyright Office for information on Fair Use limitations of U.S.
copyright law. Please refer to The Association of American Publishers’
(AAP) website for guidelines on Fair Use in the Classroom.
The Materials are for your personal use only and cannot be reformatted,
reposted, resold or distributed by electronic means or otherwise without
permission from Marcel Dekker, Inc. Marcel Dekker, Inc. grants you the
limited right to display the Materials only on your personal computer or
personal wireless device, and to copy and download single copies of such
Materials provided that any copyright, trademark or other notice appearing
on such Materials is also retained by, displayed, copied or downloaded as
part of the Materials and is not removed or obscured, and provided you do
not edit, modify, alter or enhance the Materials. Please refer to our Website
User Agreement for more details.
Order now!
Reprints of this article can also be ordered at
http://www.dekker.com/servlet/product/DOI/101081SCC100105659