3-Chloro-4-methylphenyl isocyanate → HCID 53246908、化合物

HRID 448306

反応式

HRID 448306 の反応式
Cl.[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13].[Cl:22][C:23]1[CH:24]=[C:25]([N:30]=[C:31]=[O:32])[CH:26]=[CH:27][C:28]=1[CH3:29].C(N(C(C)C)CC)(C)C>N1C=CC=CC=1>[Cl:22][C:23]1[CH:24]=[C:25]([NH:30][C:31]([NH:2][CH2:3][C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:5]=2[CH2:6][N:7]([CH:14]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]2=[O:21])[C:8]3=[O:13])=[O:32])[CH:26]=[CH:27][C:28]=1[CH3:29]

参加物

5

反応物 3

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 81531DiisopropylethylamineHCID 219885683-(4-(Aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione hydrochloride

生成物 1

HCID 53246908HCID 53246908、化合物収率 50%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
40 °C

実験手順

A mixture of 3-(4-aminomethyl-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione hydrochloride (0.50 g, 1.6 mmol), 3-chloro-4-methylphenyl isocyanate (0.26 g, 1.6 mmol) and diisopropylethylamine (0.40 g, 3.1 mmol) in 10 mL pyridine was warmed to 40° C. with stirring under N2, and the resulting solution was stirred at this temperature for 2 hours. The mixture was cooled, and the solvent was evaporated under vacuum. The residue was chromatographed, eluting with 95:5 methylene chloride-methanol, to provide 0.35 g of the product in 50% yield: mp>260° C.; 1H NMR (DMSO-d6) δ 2.00-2.04 (m, 1H), 2.22 (s, 3H), 2.36-2.43 (m, 1H), 2.57-2.64 (m, 1H), 2.86-2.98 (m, 1H), 4.36 (d, J=5.6 Hz, 2H), 4.40 (d, J=17.3 Hz, 1H), 4.54 (d, J=17.3 Hz, 1H), 5.15 (dd, J=13.1 Hz, J=5.0 Hz, 1H), 6.77 (t, J=5.6 Hz, 1H), 7.09-7.19 (m, 2H), 7.48-7.57 (m, 2H), 7.61-7.64 (m, 2H), 8.72 (s, 1H), 11.01 (s, 1H); 13C NMR (DMSO-d6) δ 18.7, 22.6, 31.2, 39.7, 46.2, 51.6, 116.5, 117.7, 121.6, 127.5, 128.3, 130.4, 131.0, 131.7, 133.0, 135.5, 139.5, 139.9, 155.1, 168.1, 171.0, 172.8; Anal. calcd for C22H21ClN4O4.0.2H2O: C, 59.45; H, 4.85; N, 12.60. Found: C, 59.28; H, 4.83; N, 12.39.

後処理

  1. stirringthe resulting solution was stirred at this temperature for 2 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated under vacuum
  4. customThe residue was chromatographed
  5. washeluting with 95:5 methylene chloride-methanol

出典と根拠

ORDレコード
ord-db0af38da2674f7699c54a8b5341a4e3
出典データセット
uspto-grants-2013_07
特許番号
US08481568B2

関連ノート

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