Diethyl Oxalate → Ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 1801904ノート

反応式

HRID 1801904 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:12](OCC)(=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)(=O)C.O>[I:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:1]2)=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 7268Diethyl OxalateHCID 666116532-Amino-4-iodobenzamide

生成物 1

HCID 136386213Ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate収率 76%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-amino-4-iodobenzamide (1.0 g, 3.61 mmol) in glacial acetic acid (10 mL) at rt was added diethyl oxalate (5 mL). The mixture was heated at 120° C. for 24 h. The mixture was cooled to rt and diluted with H2O until a precipitate formed. The precipitate was removed by filtration, washed with H2O, and dried under high vacuum for several hours to afford ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate (1.0 g, 76%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 1.36 (t, 3H), 4.48 (q, 2H), 7.90 (d, 1H), 7.95 (d, 1H), 8.20 (d, 1H), 8.28 (s, 1H), 12.78 (s, 1H); LC-MS (ESI) m/z 330 (M+H)+.

後処理

  1. temperatureThe mixture was cooled to rt
  2. customformed
  3. customThe precipitate was removed by filtration
  4. washwashed with H2O
  5. customdried under high vacuum for several hours

出典と根拠

ORDレコード
ord-9079f46b33d74e89952bc800ead3f45b
出典データセット
uspto-grants-2013_01
特許番号
US08349851B2

反応ノート

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