Facile synthesis of N-sulfonylcyclothioureas in water

Article abstract of DOI:10.1002/cjoc.201180360

A sequential one-pot synthesis of N-sulfonylcyclothioureas from N-monosulfonyl diamines, CS₂ and chloroacetic acid at room temperature in water is described. In the absence of highly toxic thiophosgene and organic solvents, this method is envir

Full text of DOI:10.1002/cjoc.201180360

FULL PAPER
Facile Synthesis of N-Sulfonylcyclothioureas in Water
Wan, Guoxiang(万国翔)
Xu, Liang(徐亮)
Ma, Xiaosi(马晓思)
Zhang, Yong(张勇)
Wang, Jian(王剑)
Zhang, Jian(张坚)
Ma, Ning*(马宁)
Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China
A sequential one-pot synthesis of N-sulfonylcyclothioureas from N-monosulfonyl diamines, CS2 and chloroace-
tic acid at room temperature in water is described. In the absence of highly toxic thiophosgene and organic solvents,
this method is environmentally benign. Simple reaction conditions, easy purification of the products, good yields
and thioglycolic acid as the useful byproduct are also important attributes of this methodology. The plausible
mechanism including tandem reactions is proposed.
Keywords sequential one-pot synthesis, N-sulfonylcyclothiourea, sulfonamides, synthetic methods, aqueous reac-
tion, tandem reactions
Introduction
at room temperature is proposed (Scheme 1).
Thioureas play important roles in medicinal chemis-
try, synthetic chemistry, supramolecular chemistry and
material chemistry.1 As a kind of derivatives of thio-
ureas, N-sulfonylcyclothioureas are also finding many
applications, with examples including drug cores, pro-
tected α,β-diamino acids and organic synthesis.2 The
reaction of sulfonyl chlorides with cyclothioureas is the
general synthetic method for N-sulfonylcyclothioureas.3
To prepare cyclothioureas, diamines are commonly
thioamidated by highly toxic thiophosgene.4 Besides,
CS2 was reported as thioamidation agent of diamines in
Scheme
N-sulfonylcyclothioureas
1
Conversion of N-monosulfonyl diamine to
R ＝ C6H5, 2-MeC6H4, 3-NO2C6H4, 4-MeC6H4, 4-ClC6H4, 4-FC6H4,
4-MeCONHC6H4, Me; A＝(CH2)2, (CH2)3, (CH2)6, 1,2-C6H4
a
few literatures.5 Another route to synthesize
Experimental
N-sulfonylcyclothioureas is through the reaction of
N-sulfonyldiamine and thiophosgene, which suffers
from the drawbacks of low yield and the use of thio-
phosgene.2a The alternative synthetic method for
N-sulfonylcyclothioureas is achieved via sulfonyl thioi-
socyanate,6 which is prepared from sulfonamide and
CS2 in the presence of SOCl2 or COCl2.7 Almost all of
the above reactions are conducted in organic or aqueous
organic solvents. Organic reactions in or on water have
attracted the attention of chemists for many years.8 Re-
cently, the synthesis of thiourea derivatives from amines
and CS2 in the presence of sodium hydroxide in water at
100 ℃ was investigated.9 Meanwhile, we reported that
reactions of aminocalixarenes with CS2, reactions of
diamines and CS2 and trisulfonamides, in the presence
of ClCH2CO2H in aqueous media afforded calixarenes
and macrocycles bearing thiourea moieties, respec-
tively.10 Herein, a sequential one-pot synthesis of
N-sulfonylcyclothioureas (2a—n) from N-monosulfonyl
diamines (1a—1n), CS2 and chloroacetic acid in water
Instruments
The melting points were obtained on a Laboratory
Devices X-4 melting apparatus and are uncorrected. IR
spectra were determined with a Perkin-Elmer 1600
1
spectrophotometer. The H NMR spectra were deter-
mined in CDCl3 or DMSO-d6 with a Bruker AVANCE
III 400 spectrometer operating at 400 MHz. The 13C
NMR spectra were determined in CDCl3, DMSO-d6 or
acetone-d6 with a Bruker AVANCE III 400 spectrome-
ter operating at 100 MHz. MS (ESI) data were obtained
on the Thermo Fisher LCQ Advantage MAX apparatus
(LC/MS). HRMS data were obtained on Bruker mi-
croOTOF-Q II instrument. Thin layer chromatography
was carried out using Merck silica gel GF254 plates. All
reagents were purchased from commercial suppliers and
used after standard procedure of purification.
Starting materials N-Monosulfonyl diamines (1)
were prepared from corresponding diamines and sul-
fonyl chlorides by the appropriate reported procedure.11
*
E-mail: mntju@tju.edu.cn; Tel.: 0086-22-27403475; Fax: 0086-22-27403475
Received April 27, 2011; revised May 19, 2011; accepted June 21, 2011.
Project supported by the National Natural Science Foundation of China (No. 20802049).
Chin. J. Chem. 2011, 29, 2081— 2085 © 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
2081

Wan et al.
FULL PAPER
Hz, 2H), 3.66 (t, J＝8.6 Hz, 2H); 13C NMR (CDCl3, 100
MHz) δ: 180.49, 140.92, 135.75, 130.49 (2C), 129.03
(2C), 49.46, 41.65; IR (KBr) ν: 3380, 1523, 1470, 1394,
1340, 1218, 1172, 1087, 1037, 828, 762, 631, 587, 545
Typical procedure for the preparation of
N-sulfonylcyclothioureas (2)
1-Phenylsulfonylimidazolidine-2-thione (2a) To
a stirred suspension of N-phenylsulfonyl ethylenamine
(1a, 0.30 g, 1.5 mmol) in water (10 mL) was added so-
dium hydroxide (0.12 g, 3.0 mmol) and carbon disulfide
(0.15 g, 2.0 mmol) at room temperature. After 5 h, so-
dium chloroacetate (0.23 g, 2.0 mmol) was added and
the reaction mixture was stirred overnight. The solid
was filtered, washed with water and hot ethyl acetate,
dried to give 2a (0.24 g, 67% yield). White solid; m.p.
＋
－1
cm ; MS (ESI) m/z: 277 [M＋H] . HRMS (ESI) calcd
for C9H9ClN2O2S2Na (M ＋ Na) ＋ 298.9686, found
298.9684.
1-(4-Fluorophenylsulfonyl)imidazolidine-2-thione
1
(2f) White solid, 73% yield; m.p. 193—194 ℃; H
NMR (DMSO-d6, 400 MHz) δ: 9.60 (s, 1H), 8.13—8.10
(m, 2H), 7.47 (t, J＝8.8 Hz, 2H), 4.23 (t, J＝8.6 Hz,
2H), 3.55 (t, J＝8.6 Hz, 2H); 13C NMR (DMSO-d6, 100
MHz) δ: 179.01, 165.55 (J＝251.5 Hz), 134.58 (J＝2.8
Hz), 132.20 (J＝9.8 Hz, 2C), 116.47 (J＝22.7 Hz, 2C),
49.61, 41.84; IR (KBr) ν: 3188, 1592, 1539, 1484, 1372,
1292, 1217, 1174, 1091, 1043, 833, 669, 595, 550, 539
1
182—183 ℃; H NMR (DMSO-d6, 400 MHz) δ: 9.54
(br s, 1H), 8.03 (d, J＝8.0 Hz, 2H), 7.74 (t, J＝7.2 Hz,
1H), 7.62 (t, J＝7.8 Hz, 2H), 4.23 (t, J＝8.6 Hz, 2H),
3.54 (t, J＝8.6Hz, 2H); 13C NMR (DMSO-d6, 100 MHz)
δ: 179.16, 138.34, 134.40, 129.28 (2C), 128.83 (2C),
49.66, 41.83; IR (KBr) ν: 3197, 1542, 1461, 1447, 1372,
＋
－1
cm ; MS (ESI) m/z: 261 (M＋H)＋. HRMS (ESI) calcd
－1
for C9H9FN2O2S2Na (M ＋ Na)
282.9982, found
1221, 1171, 1095, 1043, 721, 682, 603, 569 cm ; MS
(ESI) m/z: 243 (M＋H)＋. Anal. calcd for C9H10N2O2S2:
C 44.61, H 4.16, N 11.56; found C 44.52, H 4.29, N
11.40.
282.9985.
(3aR,7aR)-Octahydro-1-(4-methylphenylsul-
fonyl)-2H-benzimidazole-2-thione (2g) White solid,
1
75% yield; m.p. 117—119 ℃; H NMR (CDCl3, 400
1-(2-Methylphenylsulfonyl)imidazolidine-2-thione
1
MHz) δ: 7.95 (d, J＝8.4 Hz, 2H), 7.32 (d, J＝8.4 Hz,
2H), 6.84 (br s, 1H), 3.53—3.47 (m, 1H), 3.34—3.28
(m, 1H), 2.93—2.89 (m, 1H), 2.44 (s, 3H), 2.05—1.94
(m, 2H), 1.85—1.78 (m, 2H), 1.44—1.34 (m, 3H); 13C
NMR (CDCl3, 100 MHz) δ: 183.65, 145.02, 134.34,
129.28 (2C), 128.98 (2C), 70.06, 61.76, 31.09, 28.86,
24.32, 23.50, 21.71; IR (KBr) ν: 3334, 2942, 2665, 1597,
1461, 1356, 1171, 1082, 813, 715, 659, 596, 547, 527
(2b) White solid, 61% yield; m.p. 226—227 ℃; H
NMR (DMSO-d6, 400 MHz) δ: 9.54 (s, 1H), 8.01—7.99
(m, 1H), 7.60—7.56 (m, 1H), 7.43—7.40 (m, 1H),
4.29—4.25 (m, 2H), 3.65—3.60 (m, 2H), 2.54 (s, 3H);
13C NMR (DMSO-d6, 100 MHz) δ: 179.06, 137.93,
137.55, 134.03, 132.72, 131.68, 126.45, 48.67, 41.96,
20.24; IR (KBr) ν: 3335, 2985, 2971, 2093, 1594, 1520,
－1
1350, 1158, 1040, 959, 774, 693,＋665, 608, 540 cm ;
－1
＋
cm ; MS (ESI) m/z: 311 (M＋H) . Anal. calcd for
C14H18N2O2S2: C 54.17, H 5.84, N 9.02; found C 54.25,
H 5.84, N 9.01.
MS (ESI) m/z: 257 (M ＋ H) . Anal. calcd for
C10H12N2O2S2: C 46.85, H 4.72, N 10.93; found C 46.63,
H 4.80, N 10.97.
1-Phenylsulfonylhexahydropyrimidine-2-thione
1-(3-Nitrophenylsulfonyl)imidazolidine-2-thione
1
1
(2h) White solid, 78% yield; m.p. 155—157 ℃; H
(2c) Yellow solid, 66% yield; m.p. 220—221 ℃; H
NMR (Acetone-d6, 400 MHz) δ: 8.15 (br s, 1H), 7.97 (d,
J＝7.6 Hz, 2H), 7.63 (t, J＝7.6 Hz, 1H), 7.55 (t, J＝7.6
Hz, 2H), 4.17—4.14 (m, 2H), 3.38—3.34 (m, 2H),
2.20—2.14 (m, 2H); 13C NMR (DMSO-d6, 100 MHz) δ:
176.37, 133.34, 129.75, 129.06 (2C), 128.14 (2C), 46.68,
41.67, 21.69; IR (KBr) ν: 3180, 3054, 1528, 1449, 1420,
NMR (DMSO-d6, 400 MHz) δ: 8.75 (s, 1H), 8.57 (d,
J＝8.4 Hz, 1H), 8.48 (d, J＝7.6 Hz, 1H), 7.93 (t, J＝8.2
Hz, 1H), 4.30 (t, J＝8.8 Hz, 2H), 3.57 (t, J＝8.8 Hz,
2H); 13C NMR (DMSO-d6, 100 MHz) δ: 178.64, 147.78,
139.60, 134.82, 131.32, 129.01, 124.14, 49.68, 42.06;
IR (KBr) ν: 3399, 1515, 1474, 1366, 1172, 1126, 1086,
－1
－1
1322, 1246, 1164, 948, 858, 764, 688, 653, 568 cm ;
1033, 879, 674, 613, 544 cm ; MS (ESI) m/z: 288 (M
HRMS (ESI) calcd for C10H12N2O2S2Na (M＋Na)＋
＋H)＋. HRMS (ESI) calcd for C9H8N3O4S2 (M－H)－
279.0232, found 279.0229.
285.9952, found 285.9961.
1-(4-Methylphenylsulfonyl)hexahydropyrimidine-
2-thione (2i) White solid, 80% yield; m.p. 191—193
℃ (Lit.6 191—193.5 ℃); 1H NMR (CDCl3, 400 MHz)
δ: 7.86 (d, J＝8.4 Hz, 2H), 7.29 (d, J＝8.4 Hz, 2H),
6.85 (br s, 1H), 4.15—4.12 (m, 2H), 3.33—3.30 (m,
2H), 2.42 (s, 3H), 2.18—1.12 (m, 2H); 13C NMR
(CDCl3, 100 MHz) δ: 178.40, 144.37, 136.79, 129.08
(2C), 128.78 (2C), 45.99, 42.09, 21.66, 21.58; IR (KBr)
ν: 3180, 3047, 1555, 1485, 1418, 1339, 1262,－ 1174,
1-(4-Methylphenylsulfonyl)imidazolidine-2-thione
(2d) White solid, 58% yield; m.p. 224—225 ℃ (Lit.6
1
226—227 ℃); H NMR (DMSO-d6, 400 MHz) δ: 9.46
(br s, 1H), 7.91 (d, J＝8.0 Hz, 2H), 7.42 (d, J＝8.4 Hz,
2H), 4.20 (t, J＝8.6 Hz, 2H), 3.52 (t, J＝8.8 Hz, 2H);
13C NMR (DMSO-d6, 100 MHz) δ: 179.23, 145.04,
135.37, 129.71 (2C), 128.92 (2C), 49.62, 41.74, 21.57;
IR (KBr) ν: 3341, 1594, 1525, 1472,－1349, 1204, 1157,
1
1085, 1040,＋813, 665, 595, 538 cm ; MS (ESI) m/z:
1
1104, 965, 892, 806, 745, 674, 619, 547, 532 cm ; MS
257 (M＋H) .
(ESI) m/z: 271 (M＋H)＋.
1-(4-Chlorophenylsulfonyl)imidazolidine-2-thione
1
1-(4-Methylphenylsulfonyl)-1,3-diazonane-2-
thione (2j) Yellow oil, 75% yield; H NMR (CDCl3,
(2e) White solid, 40% yield; m.p. 207—209 ℃; H
1
NMR (CDCl3, 400 MHz) δ: 8.07 (d, J＝8.4 Hz, 2H),
7.52 (d, J＝8.4 Hz, 2H), 6.28 (br s, 1H), 4.31 (t, J＝8.6
400 MHz) δ: 7.75 (d, J＝8.0 Hz, 2H), 7.32 (d, J＝8.0
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© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 2081—2085

Facile Synthesis of N-Sulfonylcyclothioureas in Water
＋
Hz, 2H), 4.58 (t, J＝4.0 Hz, 1H), 3.49—3.46 (m, 2H),
2.95—2.93 (m, 2H), 2.44 (s, 3H), 1.65—1.61 (m, 2H),
1.50—1.45 (m, 2H), 1.36—1.31 (m, 4H); 13C NMR
(CDCl3, 100 MHz) δ: 182.98, 143.42, 137.09, 129.72
(2C), 127.09 (2C), 44.88, 42.97, 29.72, 29.39, 26.02,
25.68, 21.49; IR (KBr) ν: 3294,－2932, 2859, 210＋1, 1598,
C15H13N3O3S2Na (M ＋ Na)
370.0291, found
370.0291.
Results and discussion
Initially we began our investigation by choosing
N-tosylethylenediamine (1d) as the model substrate,
which reacted with CS2 and chloroacetate in sequence to
afford 1-tosylimidazoline-2-thione (2d). The reaction
time of the first step was determined by the color
change of the reaction mixtures. This solution or nearly
apparent suspension turned yellow completely 5 h after
the CS2 was dropped in, which indicated the formation
of the corresponding dithiocarbamate. The reaction time
of the second step was determined by the fully precipi-
tating of the products and the color change of the reac-
tion solution. The other reaction conditions, such as the
base, the temperature and the other halide reagents were
screened (Table 1). The results show the yields did not
increase remarkably with the rise of the temperature.
Hence, room temperature (20 ℃) is appropriate for the
reaction. The bases can be either hydroxides, such as
NaOH and KOH, or carbonates. The difference of them
is that the precipitated products were more pure when
the hydroxides were used. MeI was observed inferior to
chloroacetic acid. Moreover, other iodide, such as KI,
did not catalyze the reaction efficiently.
1
1324, 1158, 813, 664, 550 cm ; ＋HRMS (ESI ) calcd
for C14H20N2O2S2Na (M ＋ Na)
335.0858, found
335.0859.
1-Methysulfonyl-1,3-dihydro-2H-benzimidazole-
2-thione (2k) White solid, 91% yield; m.p. 162—163
℃; 1H NMR (DMSO-d6, 400 MHz) δ: 13.53 (br s, 1H),
7.81 (d, J ＝ 8.0 Hz, 1H), 7.34—7.30 (m, 1H),
7.27—7.22 (m, 2H), 3.92 (s, 3H); 13C NMR (DMSO-d6,
100 MHz) δ: 169.41, 131.42, 131.37, 125.57, 123.89,
113.87, 110.63, 41.44; IR (KBr) ν: 3096, 3019, 2923,
1619, 1510, 1450, 1414, 1364, 1296, 1262, 1171, 104＋6,
－1
971, 753, 618, 529 cm ; MS (ESI) m/z: 229 (M＋H) ＋.
HRMS (ESI) calcd for C8H8N2O2S2Na (M ＋ Na)
250.9919, found 250.9926.
1-Phenylsulfonyl-1,3-dihydro-2H-benzimidazole-
2-thione (2l White solid, 93% yield; m.p. 165—167
℃; 1H NMR (DMSO-d6, 400 MHz) δ: 13.42 (br s, 1H),
8.11—8.09 (m, 2H), 8.05—8.03(m, 1H), 7.82—7.79 (m,
2H), 7.69—7.65 (m, 1H), 7.36—7.31 (m, 2H),
7.21—7.19 (m, 1H); 13C NMR (DMSO-d6, 100 MHz) δ:
169.09, 136.98, 135.73, 131.66, 131.21, 129.83 (2C),
128.71 (2C), 126.01, 124.16, 114.01, 110.72; IR (KBr)
ν: 3036, 2962, 2920, 1591, 1505, 1450, 1382, 1292,
1260, 1－197, 1152, 1085, 1040, 746, 727, 692, 663, 583,
Table 1 Optimization of the reaction conditions
Entry Temp./℃ Basea Halideb
Yieldc/%
＋
1
545 cm ; MS (ESI) m/z: 289 (M＋H) . Anal. calcd for
C13H10N2O2S2: C 53.77, H 3.47, N 9.65; found C 53.32,
H 3.60, N 9.68.
1
2
3
4
5
6
7
8
20
50
20
20
20
40
20
20
KOH
KOH
ClCH2CO2K
ClCH2CO2K
57
63
1-(4-Methylphenylsulfonyl)-1,3-dihydro-2H-
benzimidazole-2-thione (2m) White crystal, 75%
NaOH ClCH2CO2Na
Na2CO3 ClCH2CO2Na
58
51
1
yield; m.p. 156—157 ℃; H NMR (DMSO-d6, 400
KOH
KOH
KOH
KOH
MeI
11
MHz) δ: 13.37 (br s, 1H), 8.02—7.99 (m, 1H), 7.96 (d,
J＝8.4 Hz, 2H), 7.45 (d, J＝8.4 Hz, 2H), 7.35—7.29 (m,
2H), 7.19—7.17 (m, 1H), 2.39 (s, 3H); 13C NMR
(DMSO-d6, 100 MHz) δ: 169.08, 146.73, 134.05,
131.64, 131.17, 130.24 (2C), 128.77 (2C), 125.95,
124.12, 114.02, 110.67, 21.66; IR (KBr) ν: 3147, 3105,
2985, 1596, 1494, 1436, 13－78, 1295, 1196, 1169, 1087,
MeI
16
ClCH2CO2K, KI 4 mol%
ClCH2CO2K, KI 8 mol%
58
60
a 2 equiv. b 1.3 equiv. c Isolated yield.
1
The scope of the reaction was investigated (Table 2).
Most of N-monosulfonyl diamines can be cyclized
steadily to the corresponding N-sulfonylcyclothioureas
in good to excellent yields. The products except 2j (ob-
tained as viscous yellow oil) were white or yellow pre-
cipitates. The pure products were obtained only by suc-
tion filtration and washing or recrystallization with
suitable solvents. In the substrates, some N-sulfonylaryl-
diamines could give excellent yields (Entries 11, 12),
while N-sulfonylalkyldiamines often gave lower yields
(Entries 1—7). The reaction of N-(3-aminopropyl)-
phenylsulfonamide (1h), N-(3-aminopropyl)-4-methyl-
benzenesulfonamide (1i) and N-(6-aminohexyl)-4-
methylbenzenesulfonamide (1j) with carbon disulfide
also afforded good yields (Entries 8—10). Nitro and
810, 754, 675, 578, 547 cm ; MS (ESI) m/z: 305 (M＋
H)＋. Anal. calcd for C14H12N2O2S2: C 55.24, H 3.97, N
9.20; found C 54.96, H 4.08, N 9.21.
1-(4-Acetylaminophenylsulfonyl)-1,3-dihydro-2H-
benzimidazole-2-thione (2n) White solid, 71% yield;
1
m.p. 189—191 ℃; H NMR (DMSO-d6, 400 MHz) δ:
10.48 (s, 1H), 8.01 (d, J＝8.8 Hz, 2H), 7.98—7.96 (m,
1H), 7.78 (d, J＝8.8 Hz, 2H), 7.31—7.24 (m, 2H),
7.17—7.15 (m, 1H), 2.08 (s, 3H); 13C NMR (DMSO-d6,
100 MHz) δ: 169.79, 169.18, 145.57, 132.85, 131.56,
130.33 (2C), 130.22, 125.60, 123.65, 118.71 (2C),
113.88, 111.02, 24.63; IR (KBr) ν: 3464, 3389, 3316,
1673, 1587, 1537, 1446, 1404, 1320, 1262, 1200, 1168,
－1
1092, 1047, 841, 747, 726, 660, 613, 578, 550 cm ;
MS (ESI) m/z: 348 (M＋H)＋. HRMS (ESI) calcd for
Chin. J. Chem. 2011, 29, 2081—2085
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Wan et al.
Yielda/%
78
FULL PAPER
Table 2 The scope of the reactions
Yielda/% Entry
Substrate
Entry
1
Substrate
Product
Product
67
61
66
8
9
2
3
80
75
10
4
58
11
91
5
6
7
40
73
75
12
13
14
93
75
71
a Isolated yield.
acetamido groups on the benzene ring did not affect the
cyclization (Entries 3, 14). Furthermore, N-tosyl-
(1R,2R)-diaminocyclohexane gave the corresponding
chiral product exclusively (Entry 7).
the evidence of the third step. The second and third step
is tandem process. Therefore, all the transformation is
sequential one-pot tandem reactions.
The plausible mechanism of the reactions is shown
in Scheme 2. Three steps are involved in the reactions.
Nuleophilic addition of N-monosulfonyl diamine to CS2
in water provided N-sulfoaminoethyl dithiocarbamate,
which is a nucleophile in the second step. Then the in-
tramolecular nuleophilic substitution of sulfonamide
anion and dithiocarbamate occurs in the third step.
Thioglycolic acid was recovered by acidation, extrac-
tion of the remained filtrate and fractionation under re-
duced pressure according to the reported procedure.12
This operation not only produced thioglycolic acid, an
important chemical,13 as another product, but also gave
Scheme 2 Plausible mechanism of the reactions
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© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 2081—2085

Facile Synthesis of N-Sulfonylcyclothioureas in Water
Conclusions
5
6
7
Ding, C. W.; Zhang, M. J.; Ma, N. Chin. J. Org. Chem.
2010, 30, 173 (in Chinese).
In summary, a sequential one-pot synthesis of
N-sulfonylcyclothioureas from N-monosulfonyl dia-
mines and CS2 in water was developed. In this protocol,
a variety of N-monosulfonyl diamines were converted to
the cyclization products with no need of heating, highly
toxic thiophosgene and organic solvents. The products
are easy to isolate and purify as well. Further applica-
tions of this protocol are in progress in our laboratory.
McFarland, J. W.; Kozel, T. H.; Stuhlmacher, K. R.;
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