1148
PIROZHENKO et al.
Table 3. Yields, melting points, and elemental analyses of N-arylthio-1,4-benzoquinone imines Ia e, IIIa c, e, VIIa e
and N-arylsulfonyl-1,4-benzoquinone imines IIa, e, IVa, e, VIe substituted with chlorine in the quinoid ring
Compd.
no.
mp, C (solvent
for crystallization)
Yield, %
Found S, %
Formula
Calculated S, %
Ia
Ib
Ic [10]
Id
Ie
25
21
28
32
37
76
64
23
29
16
26
73
68
64
30
23
25
27
23
153 (CH3CO2H)
9.98, 10.07
10.71, 10.80
11.07, 11.21
10.06, 10.11
9.68, 9.75
9.51, 9.64
8.91, 8.99
9.22, 9.31
9.53, 9.60
9.99, 10.04
8.79, 8.84
8.39, 8.45
7.98, 8.08
7.22, 7.36
10.20, 10.22
10.66, 10.73
11.15, 11.24
10.02, 10.08
9.71, 9.75
C13H9Cl2NO2S
C13H9Cl2NOS
C12H7Cl2NOS
C12H6Cl3NOS
C12H6Cl2N2O3S
C13H9Cl2NO4S
C12H6Cl2N2O5S
C13H8Cl3NO2S
C13H8Cl3NOS
C12H6Cl3NOS
C12H5Cl3N2O3S
C13H8Cl3NO4S
C12H5Cl3N2O5S
C12H4Cl4N2O5S
C13H9Cl2NO2S
C13H9Cl2NOS
C12H7Cl2NOS
C12H6Cl3NOS
C12H6Cl2N2O3S
10.19
10.74
11.27
10.05
9.73
9.68
8.88
9.20
9.64
10.06
8.82
8.42
8.11
7.46
10.19
10.74
11.27
10.05
9.73
184 (CH3CO2H)
186 (CH3CO2H)
168 (CH3CO2H)
262 (CH3CO2H)
123 (CH3CO2H)
135 (CH3CO2H)
169 (CH3CO2H)
220 (CH3CO2H)
203 (CH3CO2H)
256 (decomp.) (CH3CO2H)
(CH3CO2H)
IIa
IIe
IIIa
IIIb
IIIc
IIIe
IVa
IVe
VIe
VIIa
VIIb
VIIc
VIId
VIIe
(CH3CO2H)
194 (CH3CO2H)
167 (CH3CO2H)
109 (CH3CO2H)
213 (n-C7H16)
217 (n-C7H16)
171 (CH3CO2H)
N-Arylthio-1,4-benzoquinone imines Ia e, IIIa e,
VIIa e substituted with chlorine in the quinone ring.
To suspension of 2 mmol of chloro-substituted
p-aminophenol in 20 ml of anhydrous ethyl ether
were added equimolar amounts of an appropriate aryl-
sulfonyl chloride and triethylamine. The arising
precipitate of triethylamine hydrochloride was filtered
off, the filtrate was evaporated in a vacuum of a
water-jet pump. The precipitate of N-arylthio-1,4-
benzoquinone imine formed was washed with
methanol and acetic acid.
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