Reaction of acids and diacids with aroxy(alcoxy)sulfonyl isocyanates: Synthesis of N-acylsulfamates, disulfamates, and N,N′-disulfonylureas

Article abstract of DOI:10.1080/00397910802219114

Reaction of carboxylic acids with aroxy(alcoxy)sulfonylisocyanates allowed the preparation of the corresponding aroxy(alcoxy) N-acylsulfamates. With succinic diacid, the same reaction yielded the corresponding N, N′-diacylsulfamates, whereas the N, N′-dis

Full text of DOI:10.1080/00397910802219114

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Reaction of Acids and Diacids
with Aroxy(alcoxy)sulfonyl
Isocyanates: Synthesis of N-
Acylsulfamates, Disulfamates,
and N,N′-Disulfonylureas
Hassen Sbihi a , Mohamed Beji a & Ahmed Baklouti a
a Laboratory of Structural Organic Chemistry,
Department of Chemistry , Faculty of Sciences of
Tunis , Tunis, Tunisia
Published online: 09 Sep 2008.
To cite this article: Hassen Sbihi , Mohamed Beji & Ahmed Baklouti (2008) Reaction
of Acids and Diacids with Aroxy(alcoxy)sulfonyl Isocyanates: Synthesis of N-
Acylsulfamates, Disulfamates, and N,N′-Disulfonylureas, Synthetic Communications:
An International Journal for Rapid Communication of Synthetic Organic Chemistry,
38:15, 2490-2498, DOI: 10.1080/00397910802219114
To link to this article: http://dx.doi.org/10.1080/00397910802219114
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Synthetic Communications1, 38: 2490–2498, 2008
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910802219114
Reaction of Acids and Diacids with
Aroxy(alcoxy)sulfonyl Isocyanates: Synthesis
of N-Acylsulfamates, Disulfamates, and
N,N0-Disulfonylureas
Hassen Sbihi, Mohamed Beji, and Ahmed Baklouti
1Laboratory of Structural Organic Chemistry, Department of Chemistry, Faculty
of Sciences of Tunis, Tunis, Tunisia
Abstract: Reaction of carboxylic acids with aroxy(alcoxy)sulfonylisocyanates
allowed the preparation of the corresponding aroxy(alcoxy) N-acylsulfamates.
With succinic diacid, the same reaction yielded the corresponding N, N0-diacylsul-
famates, whereas the N, N0-disulfonylureas were obtained by reaction of maleic or
fumaric diacids.
Keywords: Acids, aroxy(alkoxy)sulfonylisocyanates, diacids, N-acylsulfamates,
N, N0-diacyldisulfamates, N,N0-disulfonylureas
INTRODUCTION
Aroxy(alkoxy)sulfonylisocyanates may be considered interesting inter-
mediates in the synthesis of ureas,[1] carbamates,[2] cyclic b-lactams,[3,4]
and as precursors for sulfonamides,[5] which are widely used in the prep-
aration of some pharmacological products. We have previously reported
the reaction of these isocyanates with adamantyl alcohols,[6] alkyl (aryl)
magnesium bromides,[7] and highly fluorinated alcohols,[8] thiols,[8]
diols,[9] and aminoalcohols.[10]
In the present work, we describe the reaction of acids and diacids
with the same starting sulfonyl heterocumelenes. With acids, the addition
Received in the U.K. July 2, 2007
Address correspondence to Ahmed Baklouti, Laboratory of Structural
Organic Chemistry, Department of Chemistry, Faculty of Sciences of Tunis,
Tunis, Tunisia. E-mail: adam.sbihi@yahoo.com
2490

Reaction of Acids and Diacids
2491
Scheme 1. Synthesis of N-acylsulfamates.
reaction followed by decarboxylation allows the preparation of the
corresponding N-acylsulfamates. However, with diacids, the reaction
leads either to disulfamates or to N, N0-disulfonylureas, depending upon
the nature of the starting diacid.
RESULTS AND DISCUSSION
The addition of octanoic, benzoic, or 3-methylbut-1-ene-oic acids to
aroxy(alkoxy)sulfonylisocyanates 1a–e has been carried out in toluene
at room temperature (Scheme 1). The addition products were not
isolated, and only the corresponding N-acylsulfamates (decarboxylated
products) were obtained with good yields.
These N-acylsulfamates, which may have interesting biological and
antitumor properties as do simple and N-alkylated ones, can be prepared
by direct acylation of sulfamates.[7] The reaction, in this case, was much
more difficult and yields were generally lower.
At higher temperature (60 ꢀC), the reaction occurred more rapidly,
but yields were decreased as shown in Table 1. For compounds 2a, 3a,
and 4a obtained from the 2,4,6-trimethylaroxysulfonyl isocyanate
Table 1. Preparation of N-Acylsulfamates 2a–c, 3a–c, and 4a,b,e
Time Yield Time Yield
(min)a (%)a (min)b (%)b
Product
R
R0
2a
2b
2c
3a
3b
3c
4a
4b
4e
2,4,6-Trimethyphenyl
2,2,2-Trichloroethyl
4-Chlorophenyl
2,4,6-Trimethyphenyl
2,2,2-Trichloroethyl
4-Chlorophenyl
2,4,6-Trimethyphenyl
2,2,2-Trichloroethyl
4-Nitrophenyl
CH3(CH2)6
CH3(CH2)6
CH3(CH2)6
Phenyl
Phenyl
Phenyl
120
30
30
120
30
30
60
77
82
95
60
73
85
74
88
97
60
20
20
60
20
20
30
20
20
70
75
90
50
70
80
66
80
80
=
CH3(CH3)C CH
=
CH3(CH3)C CH
30
30
CH3(CH3)C ¼ CH
aReactions carried out at room temperature.
bAt 60 ꢀC.

2492
H. Sbihi, M. Beji, and A. Baklouti
Scheme 2. Synthesis of N,N0-diacyldisulfamates.
(electrodonor ring substituents), the reaction rates were longer and yields
were lower (see Table 1).
At room temperature, the same addition reaction followed by decar-
boxylation occurred the by action of 1 equivalent of succinic acid on 2
equivalents of aroxy(alkoxy)sulfonylisocyanates.
As shown in Scheme 2, the corresponding N, N0-diacyldisulfamates
were obtained. These products are described for the first time.
In the same conditions as for succinic acid and aroxy(alkoxy)sulfonyl-
isocyanates, the reaction of maleic and fumaric acids in one pot prepares
diaroxy (alkoxy) disulfonylureas (Scheme 3).
For maleic acid, this result may be interpreted according to the
mechanism shown in Scheme 3.
The addition of 1 equivalent of maleic acid to 2 equivalents of
aroxy(alkoxy)sulfonylisocyanates is followed by the elimination of two
carbon dioxide molecules (Scheme 3). The resulting unstable intermediate
(I) proceeds via a concerted cyclic mechanism (II) to give, after elimi-
nation of carbon oxide and acetylene, the corresponding N, N0-diaroxy-
(alkoxy)-N,N0-disulfonylureas. The presence of acethylene was further
confirmed using the water solution bromine decolorization test.
The same ureas were obtained by action of fumaric acid. As shown in
Table 2, the yields were slightly lower. This may be explained if we
assume that the carbon–carbon double bond character (II) is decreased
enough by mesomeric effect (presence of CO and SO2 electron-attracting
groups), leading to a possible isomerization of E to Z. Thus, the con-
certed cyclic mechanism becomes possible.
Scheme 3. Proposed mechanism for the formation of N,N0-disulfonylureas.

Reaction of Acids and Diacids
2493
Table 2. Preparation of disulfamates 5a–c and ureas 6a,b,e
Product
R
Time (min)
Yield (%)
5a
5b
5c
6a
2,4,6-Trimethyphenyl
2,2,2-Trichloroethyl
4-Chlorophenyl
60
30
25
60
84
90
95
78a
70b
96a
75b
95a
86b
2,4,6-Trimethyphenyl
6b
6e
2,2,2-Trichloroethyl
4-Nitrophenyl
30
20
aYield with maleic acid.
bYield with fumaric acid.
CONCLUSION
Reaction of carboxylic acids with chlorosulfonylisocyanates was reported
to produce N-chlorosulfonylamid.[11] Subsequent treatment of the latter
with triethylamine afforded the corresponding nitriles with elimination of
HCl and SO3. This allowed a two-step transformation of acids to nitriles.
In our case, the addition reaction of acids to aroxy(alkoxy)sulfonyl-
isocyanates followed by decarboxylation may be considered a one-pot
aroxy(alcoxy) sulfamylation. To study the properties of well-known acids
such as aspirin, trifluoroacetic acid, and other large-scale acids, the
extension of this reaction to such acids is in progress.
EXPERIMENTAL
IR spectra were obtained using a Perkin Elmer FT-Paragon. NMR spectra
were recorded on a Bruker AC 300 spectrometer at 300 and 75MHz for 1H
and 13C respectively. Chemical shifts were reported in parts per million from
internal TMS for 1H and 13C. High resolution mass spectra (HRMS) were
obtained by negative mode of electrospray ionization (ESI NEG) with a
Finningan MAT SBE spectrometer.
Aroxy(alkoxy)sulfonylisocyanates 1a–e were prepared according to
literature methods.[12,13]
General Procedure for the Synthesis of Products 2–6
To a solution of acid (10 mmol) or diacid (5 mmol) and triethylamine
(0.1 mmol) in anhydrous toluene, 10 mmol of aroxy(alcoxy)

2494
H. Sbihi, M. Beji, and A. Baklouti
sulfonylisocyanate dissolved in the same solvent were added under argon.
The mixture was stirred at room temperature for 30–120 min (or at heat
to 60 ꢀC for 20–60 min) for acids and at room temperature for 20–60 min
for diacids. After filtration, the solid was recrystallized from CCl4.
Data
(2,4,6-Trimethylphenyl)-N-(octanoyl)sulfamate (2a)
Mp: 60 ꢀC. IR (CHCl3): n ¼ 3375 (NH), 1736 (CO), 1384, 1180
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 11–10.5 (1H, NH), 6.9
(s, 2H, aromatic H), 2.5 (t, 2H, CH2CO, 3J ¼ 7.5 Hz), 2.4 (s, 6H, ArCH3),
2.2 (s, 3H, ArCH3), 1.65 (m, 2H, COCH2CH2), 1.3 (m, 8H, CH3 (CH2)4),
0.9 (t, 3H, CH2 CH3, 3J ¼ 6.2 Hz). 13C NMR (CD3COCD3=TMS):
d ¼ 171.2 (CO), 146.4, 137.2, 132.2, 130.4 (ArC), 36.6 (CH2CO), 32.3,
29.8, 29.3, 24.9 [(CH2)4], 23.1 (CH2CH3), 20.6, 17.2 (ArCH3), 14.3
(CH2CH3). HRMS (ESI): m=z ¼ (%): 340.4 [(M ꢁ 1)ꢁ, 100].
(2,2,2-Trichloroethyl)-N-(octanoyl)sulfamate (2b)
Mp: 90 ꢀC. IR (CHCl3): n ¼ 3375 (NH), 1729 (CO), 1384, 1167
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 11.2–10.9 (1H, NH), 5
3
(s, 2H, CCl3 CH2O), 2.45 (t, 2H, CH2CO, J ¼ 8.1 Hz), 1.65 (m, 2H,
COCH2CH2), 1.3 [m, 8H, CH3(CH2)4), 0.9 (t, 3H, CH2CH3, 3J ¼ 6.8 Hz).
Hz). 13C NMR (CD3COCD3=TMS): d ¼ 172.1 (CO), 94.1 (CCl3), 81
(CCl3CH2), 36.6 (CH2CO), 32.3, 29.7, 29.4, 24.9 [(CH2)4], 23.1 (CH2CH3),
14.3 (CH2CH3). HRMS (ESI): m=z ¼ (%) 353.6 [(M ꢁ 1)ꢁ, 100].
(4-Chlorophenyl)-N-(octanoyl)sulfamate (2c)
Mp: 98 ꢀC. IR (CHCl3): n ¼ 3383 (NH), 1740 (CO), 1376, 1180 (SO2) cmꢁ1.
1H NMR (CD3COCD3=TMS): d ¼ 11.2–10.5 (1H, NH), 7.5–7.2 (m, 4H,
aromatic H), 2.4 (t, 2H, COCH2, 3J ¼ 8.2 Hz), 1.65 (m, 2H, COCH2CH2),
3
1.3 [m, 8H, CH3(CH2)4], 0.9 (t, 3H, CH2CH3, J ¼ 6.8 Hz). 13C NMR
(CD3COCD3=TMS): d ¼ 171.4 (CO), 149.4, 133.4, 130.7, 124.4 (ArC),
36.5 (CH2CO), 32.2, 29.8, 29.5, 25 [(CH2)4], 23.1 (CH2CH3), 14.2 (CH2CH3).
HRMS (ESI): m=z ¼ (%) 332.8 [(M ꢁ 1)ꢁ, 100].
(2,4,6-Trimethylphenyl)-N-(benzoyl)sulfamate (3a)
Mp: 132 ꢀC. IR (CHCl3): n ¼ 3394 (NH), 1719 (CO), 1376, 1182
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 11.5–11 (1H, NH), 8–
7.3 (m, 5H, aromatic H), 6.8 (s, 2H, aromatic H), 2.3 (s, 6H, ArCH3),

Reaction of Acids and Diacids
2495
2.2 (s, 3H, ArCH3). 13C NMR (CD3COCD3=TMS): d ¼ 165.6 (CO),
146.8, 137.5, 133.7, 132.6, 130.7, 130, 129.2 (ArC), 20.7, 17.5 (ArCH3).
HRMS (ESI): m=z ¼ (%) 318.3 [(M ꢁ 1)ꢁ, 100].
(2,2,2-Trichloroethyl)-N-(benzoyl)sulfamate (3b)
Mp: 120 ꢀC. IR (CHCl3): n ¼ 3398 (NH), 1711 (CO), 1376, 1183
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 11.5 (1H, NH), 8– 7.5
(m, 5H, aromatic H), 5.2 (s, 2H, CCl3CH2O). 13C NMR
(CD3COCD3=TMS): d ¼ 165.9 (CO), 134.3, 129.1, 130.9, 129.8 (ArC),
94.3 (CCl3), 81.3 (CCl3CH2). HRMS (ESI): m=z ¼ (%): 331.5
(M ꢁ 1)ꢁ, (100).
(4-Chlorophenyl)-N-(benzoyl)sulfamate (3c)
Mp: 125 ꢀC. IR (CHCl3): n ¼ 3400 (NH), 1724 (CO), 1376, 1180
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 12–11 (1H, NH), 8–7.5
(m, 5H, aromatic H), 7.5–7 (m, 4H, aromatic H). 13C NMR
(CD3COCD3=TMS): d ¼ 165.2 (CO), 133.9, 133.5, 130.3, 129.9, 129.8,
128.4, 123.5 (ArC). HRMS (ESI): m=z ¼ (%): 310.7 (M ꢁ 1)ꢁ, (100).
(2,4,6-Trimethylphenyl)-N-(3-methylbut-2-enoyl)sulfamate (4a)
ꢀ
=
Mp: 100 C. IR (CHCl3): n ¼ 3386 (NH), 1718 (CO), 1637 (C C), 1379,
1181 (SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 10.7 (1H, NH), 6.9
1
=
(s, 2H, aromatic H), 5.9 (s, 1H, CH C), 2.3 (s, 6H, ArCH3), 2.25 (s, 3H,
=
CH3C CH), 2.2 (s, 3H, ArCH3), 1.9 (s, 3H, CH3C CH). 13C NMR
=
=
(CD3COCD3=TMS): d ¼ 163.5 (CO), 160.5 (CH C(CH3)2), 146.5,
=
137.2, 132.3, 130.5 (ArC), 116.5 [C(O)C C], 27.6 (CH3C C), 20.6
=
=
(ArCH3), 20.5 (CH3C C), 17.2 (ArCH3). HRMS (ESI): m=z ¼ (%)
296.3 [(M ꢁ 1)ꢁ, 100].
(2,2,2-Trichloroethyl)-N-(3-methylbut-2-enoyl)sulfamate (4b)
ꢀ
=
Mp: 85 C. IR (CHCl3): n ¼ 3386 (NH), 1710 (CO), 1630 (C C), 1379,
1181 (SO2) cmꢁ1. 1H NMR (CD3COCD3=TMS): d ¼ 10.5 (1H, NH),
=
=
5.9 (s, 1H, CH C), 5.1 (s, 2H, CCl3CH2O), 2.2 (s, 3H, CH3C CH), 1.9
=
(s, 3H, CH3C CH). 13C NMR (CD3COCD3=TMS): d ¼ 163 (CO), 161.1
=
[C(O)CH C, 116.3 (C C(CH3)2], 92.1 (CCl3), 76.4 (CCl3CH2), 27.6, 20.5
=
ꢁ
=
(C C(CH3)2]. HRMS (ESI): m=z ¼ (%) 309.5 [(M ꢁ 1) , 100].

2496
H. Sbihi, M. Beji, and A. Baklouti
(4-Nitrophenyl)-N-(3-methylbut-2-enoyl)sulfamate (4e)
ꢀ
=
Mp: 107 C. IR (CHCl3): n ¼ 3392 (CO), 1722 (CO), 1642 (C C), 1380,
1183 (SO2) cmꢁ1. 1H NMR (CD3COCD3=TMS): d ¼ 8.6–7.6 (m, 4H,
=
=
aromatic H), 7.5 (1H, NH), 5.9 (s, 1H, C CH), 2.2 (s, 3H, CH3C CH),
=
1.9 (s, 3H, CH3C CH). 13C NMR (CD3COCD3=TMS): d ¼ 163.4
(CO), 162 [CH ¼ C(CH3)2), 155, 147.2, 126.1, 123.8 (ArC), 115.9
=
[C(O)CH ¼ C], 27.7, 20.6 [CH C(CH3)2). HRMS (ESI): m=z ¼ (%)
299.2 [(M ꢁ 1)ꢁ, 100].
Di-(2,4,6-Trimethylphenylsulfamate)butandioyl (5a)
Mp: 145 ꢀC. IR (CHCl3): n ¼ 3302 (NH), 1753 5CO), 1379, 1210
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 7.1 (2H, 2NH), 6.9 (s,
4H, aromatic H), 2.6 (s, 4H, COCH2CH2CO), 2.35 (s, 12H, ArCH3),
2.24 (s, 6H, ArCH3). 13C NMR (CD3COCD3=TMS): d ¼ 173.9 (CO),
146.4, 137.6, 132.7, 130.6 (ArC), 30.6 (CH2) 20.6, 17.3 (ArCH3). HRMS
(ESI): m=z ¼ (%) 510.5 [(M ꢁ 2)ꢁ, 100].
Di-(2,2,2-Trichloroethylsulfamate)butandioyl (5b)
Mp: 109 ꢀC. IR (CHCl3): n ¼ 3360 (NH), 1776 (CO), 1400, 1164
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 7.2 (2H, 2NH), 4.9 (s,
4H, CCl3CH2O), 2.6 (s, 4H, COCH2CH2CO). 13C NMR
(CD3COCD3=TMS): d ¼ 171.2 (CO), 95.4 (CCl3), 75.8 (CCl3CH2), 30.5
(CH2). HRMS (ESI): m=z ¼ (%) 537 [(M ꢁ 2)ꢁ, 100].
Di-(4-Chlorophenylsulfamate)butandioyl (5c)
Mp 115 ꢀC. IR (CHCl3): n ¼ 3351 (NH), 1749 (CO), 1402, 1176
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 8 (2H, 2NH), 8–7 (m,
8H, aromatic H), 2.6 (s, 4H, COCH2CH2CO). 13C NMR
(CD3COCD3=TMS): d ¼ 174 (CO), 146.4, 133.5, 130.4, 124.8 (ArC),
31.2 (CH2). HRMS (ESI): m=z ¼ (%) 495.3 [(M ꢁ 2)ꢁ, 100].
N,N0-(2,4,6-Trimethylphenoxysulfonyl)ureas (6a)
Mp: 125 ꢀC. IR (CHCl3): n ¼ 3351 (NH), 1749 (CO), 1402, 1176
(SO2) cmꢁ1. 1H NMR (CD3COCD3=TMS): d ¼ 7 (2H, 2NH), 6.9 (s,
4H, aromatic H), 2.35 (s, 12H, ArCH3), 2.2 (s, 6H, ArCH3). 13C NMR

Reaction of Acids and Diacids
2497
(CD3COCD3=TMS): d ¼ 146.1 (CO), 145.9, 136.3, 131.7, 130 (ArC),
20.6, 17 (ArCH3). HRMS (ESI): m=z ¼ (%) 454.5 [(M ꢁ 2)ꢁ, 100].
N,N0-(2,2,2-Trichloroethoxysulfonyl)ureas (6b)
Mp: 102 ꢀC. IR (CHCl3): n ¼ 3370 (NH), 1776 (CO), 1400, 1163
1
(SO2) cmꢁ1. H NMR (CD3COCD3=TMS): d ¼ 5.1 (s, 4H, CCl3CH2O).
13C NMR (CD3COCD3=TMS): d ¼ 147.6 (CO), 94 (CCl3), 81.3
(CCl3CH2). HRMS (ESI): m=z ¼ (%) 480.9 [(M ꢁ 2)ꢁ, 100].
N,N0-(4-Nitrophenoxysulfonyl)ureas (6e)
Mp: 123 ꢀC. IR (CHCl3): n ¼ 3351, 1749, 1402, 1176 cmꢁ1. 1H NMR
(CD3COCD3=TMS): d ¼ 8.5–7.5 (m, 8H),
8
(2H). 13C NMR
(CD3COCD3=TMS): d ¼ 154 (CO), 147.26, 131.9, 126.6, 123.9 (ArC).
HRMS (ESI): m=z ¼ (%) 460.3 [(M ꢁ 2)–, 100].
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`
´
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