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Ethyl chloroacetate → 3-(2-chlorophenyl)-1-ethoxycarbonylmethyl-6-ethoxycarbonyl-5,7-dimethyl-2,4(1H,3H)-quinazolinedione

HRID 1995645
ノート
印刷プレビュー

反応式

HRID 1995645 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([CH3:27])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=2[CH3:21])[NH:12][C:11]1=[O:28].Cl[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([CH3:27])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=2[CH3:21])[N:12]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:11]1=[O:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 1336033-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-2,4(1H,3H)-quinazolidinedione

生成物 1

HCID 128557123-(2-chlorophenyl)-1-ethoxycarbonylmethyl-6-ethoxycarbonyl-5,7-dimethyl-2,4(1H,3H)-quinazolinedione収率 62.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

A portion (50 mg) of sodium hydride suspension (50%) in mineral oil was added to a stirred solution of 3-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-2,4-(1H,3H)-quinazolinedione (373 mg) in dried dimethylformamide (20 ml). After addition of ethyl chloroacetate (123 mg), the mixture was stirred at 70° C. for one hour. The solvent was evaporated at reduced pressure, and the residue was extracted with CHCl3, and the CHCl3 extract was washed with water, dried over anhydrous MgSO4 and concentrated. The residue was recrystallized from ethanol to give 3-(2-chlorophenyl)-1-ethoxycarbonylmethyl-6-ethoxycarbonyl-5,7-dimethyl-2,4(1H,3H)-quinazolinedione (287 mg, 62.6%) melting at 158°-159° C. MS: m/e, 458(M+), 423. NMR: δ (ppm, CDCl3), 1.28 (3H, t), 1.39 (3H, t), 2.40 (3H, s), 2.74 (3H, s), 4.28 (2H, q), 4.42 (2H, q), 4.92 (2H, s), 6.74 (1H, s), 7.41 (4H, m).

後処理

  1. customThe solvent was evaporated at reduced pressure
  2. extractionthe residue was extracted with CHCl3
  3. extractionthe CHCl3 extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-ce5df807dc274bdeab3cf460fdb5b470
出典データセット
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04405623

反応ノート

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