Phenyl isocyanate → N-benzyl-4-methyl-2-(3-phenylureido)thiazole-5-carboxamide

HRID 45369ノート

反応式

HRID 45369 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.C(OCC)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:32]([NH:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:33])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

生成物 1

HCID 16897025N-benzyl-4-methyl-2-(3-phenylureido)thiazole-5-carboxamide収率 80%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.10 g, 0.40 mmol) in anhydrous tetrahydrofuran (5 mL), triethylamine (0.17 mL, 0.12 g, 1.22 mmol) and phenyl isocyanate (0.07 mL, 0.072 g, 0.61 mmol) were added dropwise at ambient temperature. The reaction mixture was stirred at ambient temperature for 25 h and then diluted with ethyl ether (20 mL). The white precipitate obtained was collected by filtration, washed with ethyl ether (3×6 mL) and dried under the reduced pressure to afford the title compound as a white solid in 80% yield (0.119 g); m.p.>300° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.00 (s, 1H), 8.47 (t, J=5.7 Hz, 1H), 7.46-7.17 (m, 10H), 7.03-6.98 (m, 1H), 4.35 (d, J=6.0 Hz, 2H), 2.43 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 162.2, 140.2, 140.0, 129.4, 129.2, 128.7, 127.7, 127.1, 123.3, 119.1, 118.6, 43.0, 39.1; MS (ES+) m/z 367.2 (M+1).

後処理

  1. customThe white precipitate obtained
  2. filtrationwas collected by filtration
  3. washwashed with ethyl ether (3×6 mL)
  4. customdried under the reduced pressure

出典と根拠

ORDレコード
ord-0366db3439354bc9903b6221769da6d2
出典データセット
uspto-grants-2013_09
特許番号
US08541457B2

反応ノート

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