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

HRID 1995645
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HRID 1995645 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ce5df807dc274bdeab3cf460fdb5b470
출처 데이터셋
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04405623

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