NEW SYNTHESIS OF 2-OXOALKANAMIDE OXIMES
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N-(2,4-Dimethoxyphenyl)-2-(hydroxyimino)-
acetamide (5f). Yield 57%, mp 175–177°C. H NMR
(2H, CH2, J = 6.0), 6.89 t (1H, Harom, J = 7.6), 6.96 d
(1H, Harom, J = 8.4), 7.14 d (1H, Harom, J = 7.6), 7.22 t
(1H, Harom, J = 8.4), 7.50 s (1H, CH=N), 8.25 br.s
(1H, NH), 11.83 s (1H, OH). Found, %: C 57.48;
H 5.62; N 13.35. C10H12N2O3. Calculated, %: C 57.69;
H 5.81; N 13.45.
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spectrum, δ, ppm (J, Hz): 3.74 s (3H, CH3O), 3.83 s
(3H, CH3O), 6.50 d.d (1H, Harom, J = 8.8, 2.4), 6.64 d
(1H, Harom, J = 2.4), 7.59 s (1H, CH=N), 7.92 d (1H,
Harom, J = 8.8), 8.95 s (1H, NH), 12.15 s (1H, OH).
Found, %: C 53.68; H 5.52; N 12.35. C10H12N2O4.
Calculated, %: C 53.57; H 5.39; N 12.49.
N,N′-(1,4-Phenylene)bis[2-(hydroxyimino)acet-
amide] (5n). Yield 43%, mp >300°C; published data
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[17]: mp >285°C. H NMR spectrum, δ, ppm (J, Hz):
2-(Hydroxyimino)-N-(2-iodophenyl)acetamide
(5g). Yield 67%, mp 163–165°C; published data [14]:
7.61 s (4H, Harom), 7.62 s (2H, N=CH), 9.99 br.s (2H,
NH), 12.00 br.s (2H, OH).
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mp 167–168°C. H NMR spectrum, δ, ppm (J, Hz):
6.96 t (1H, Harom, J = 7.6), 7.39 t (1H, Harom, J = 7.6),
7.60 s (1H, CH=N), 7.78 d (1H, Harom, J = 8.0), 7.87 d
(1H, Harom, J = 8.0), 9.28 s (1H, NH), 12.35 s
(1H, OH).
2-(Hydroxyimino)-N-(1,3-thiazol-2-yl)acetamide
(5o). Yield 63%, mp 223–225°C. H NMR spectrum,
δ, ppm (J, Hz): 7.32 s and 7.56 s (1H each, 4-H, 5-H),
7.85 s (1H, CH=N), 10.42 br.s (1H, NH), 12.51 br.s
(1H, OH). Found, %: C 35.31; H 2.81; N 24.35.
C5H5N3O2S. Calculated, %: C 35.08; H 2.94; N 24.55.
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2-(Hydroxyimino)-N-[2-(trifluoromethyl)phenyl]-
acetamide (5h). Yield 91%, mp 82–84°C; published
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data [15]: 79–80°C. H NMR spectrum, δ, ppm
N-(1,3-Benzothiazol-2-yl)-2-(hydroxyimino)-
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(J, Hz): 7.43 t (1H, Harom, J = 7.6), 7.63 s (1H, CH=N),
7.67–7.74 m (2H, Harom), 7.73 d (1H, Harom, J = 7.6),
7.79 d (1H, Harom, J = 8.0), 9.41 s (1H, NH), 12.30 s
(1H, OH).
acetamide (5p). Yield 22%, mp 220–223°C. H NMR
spectrum, δ, ppm (J, Hz): 7.34 t (1H, Harom, J = 7.7),
7.47 t (1H, Harom, J = 8.8), 7.78 d (1H, Harom, J = 8.8),
7.87 s (1H, CH=N), 8.02 d (1H, Harom, J = 8.8),
10.54 br.s (1H, NH), 12.70 br.s (1H, OH). Found, %:
C 48.71; H 3.08; N 18.75. C9H7N3O2S. Calculated, %:
C 48.86; H 3.19; N 18.99.
N-(2,6-Dimethylphenyl)-2-(hydroxyimino)acet-
amide (5i). Yield 42%, mp 186–188°C. 1H NMR spec-
trum, δ, ppm (J, Hz): 2.25 s (3H, CH3), 2.13 s (6H,
CH3), 7.04–7.10 m (3H, Harom), 7.61 s (1H, CH=N),
8.38 br.s (1H, NH), 11.98 br.s (1H, OH). Found, %:
C 62.60; H 6.22; N 14.50. C10H12N2O2. Calculated, %:
C 62.49; H 6.29; N 14.57.
2-Hydroxyimino-N-(2-phenylethyl)acetamide
(5q). After addition of water, the mixture was extracted
with ethyl acetate (3×20 mL). The combined extracts
were washed with water and dried over sodium sulfate,
the solvent was distilled off under reduced pressure,
and the residue was purified by column chromatog-
raphy using chloroform–methanol (10:1) as eluent.
Yield 55%, mp 123–125°C. 1H NMR spectrum, δ, ppm
(J, Hz): 2.73 t (2H, CH2, J = 7.2), 3.20–3.34 m (2H,
CH2), 7.16–7.29 m (5H, Harom), 7.50 s (1H, CH=N),
8.25 br.s (1H, NH), 11.83 s (1H, OH). Found, %:
C 62.32; H 6.18; N 14.45. C10H12N2O2. Calculated, %:
C 62.49; H 6.29; N 14.57.
N-(2,5-Dibromophenyl)-2-(hydroxyimino)acet-
amide (5j). Yield 78%, mp 148–150°C. 1H NMR spec-
trum, δ, ppm (J, Hz): 7.33 d.d (1H, Harom, J = 8.8, 2.4),
7.64 d (1H, Harom, J = 8.8), 7.66 s (1H, Harom), 8.16 s
(1H, CH=N), 9.46 s (1H, NH), 12.52 s (1H, OH).
N-(3,5-Dibromophenyl)-2-(hydroxyimino)acet-
amide (5k). Yield 79%, mp 196–198°C; published
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data [16]: mp 197–200°C. H NMR spectrum, δ, ppm
(J, Hz): 7.49 t (1H, Harom, J = 1.6), 7.59 s (1H, CH=N),
7.95 d (2H, Harom, J = 1.6), 10.33 br.s (1H, NH).
N-Cyclohexyl-2-(hydroxyimino)acetamide (5r).
Yield 47%, mp 155–157°C. 1H NMR spectrum, δ, ppm
(J, Hz): 1.21–1.28 m and 1.53–1.74 m (5H each,
C6H11), 3.55–3.65 m (1H, CH–N), 7.43 s (1H, CH=N),
7.76 br.s (1H, NH), 11.7 s (1H, OH). Found, %:
C 56.32; H 8.28; N 16.35. C8H14N2O2. Calculated, %:
C 56.45; H 8.29; N 16.46.
Ethyl 4-{[2-(hydroxyimino)acetyl]amino}ben-
zoate (5l). Yield 81%, mp 189–191°C; published data
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[12]: mp 185°C. H NMR spectrum, δ, ppm (J, Hz):
1.30 t (3H, CH3, J = 7.2), 4.28 q (2H, CH2, J = 7.2),
7.69 s (1H, CH=N), 7.82 d (2H, Harom, J = 8.8), 7.90 d
(2H, Harom, J = 8.8), 10.44 br.s (1H, NH), 12.17 s
(1H, OH).
N-Butyl-2-(hydroxyimino)acetamide (5s) was
isolated as described above for 5q. Yield 67%, yel-
lowish oil. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz):
0.93 t (3H, CH3, J = 7.5), 1.34–1.39 m (2H, CH2),
1.50–1.55 m (2H, CH2), 3.31 d.d (2H, CH2, J = 13.3,
2-(Hydroxyimino)-N-(2-methoxybenzyl)acet-
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amide (5m). Yield 41%, mp 133–135°C. H NMR
spectrum, δ, ppm (J, Hz): 3.80 s (3H, CH3O), 4.32 d
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 4 2019