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1,1'-Carbonyldiimidazole → (2-Oxo-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl 4-methylbenzenesulfonate

HRID 896011
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HRID 896011 반응식
[NH2:1][C:2]1[C:7]2[NH:8][CH:9]([CH2:12][O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>C(Cl)Cl>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([O:13][CH2:12][CH:9]2[N:8]3[C:33](=[O:34])[NH:1][C:2]4=[CH:3][CH:4]=[CH:5][C:6](=[C:7]34)[O:11][CH2:10]2)(=[O:16])=[O:15])=[CH:18][CH:19]=1
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참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 20814150Toluene-4-sulfonic acid 5-amino-3,4-dihydro-2H-benzo[1,4]oxazin-3-ylmethyl ester

생성물 1

HCID 22349481(2-Oxo-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl 4-methylbenzenesulfonate수율 55.5%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

Toluene-4-sulfonic acid 5-amino-3,4-dihydro-2H-benzo[1,4]oxazin-3-ylmethyl ester (6.7 g , ˜10 mmole) was dissolved in methylene chloride (100 mL), N, N-diisopropylethylamine (5.22 mL, 30.0 mmole) was added, followed by carbonyldiimidazole (4.05 g, 25.0 mmole), and the mixture was stirred at room temperature under nitrogen overnight. The mixture was diluted with methylene chloride (100 mL), washed with water (2×200 mL), saturated sodium bicarbonate (200 mL) saturated sodium chloride (200 mL) and dried (Na2SO4). Filtration, evaporation in vacuum and column chromatography on silica gel with 1% methanol/methylene chloride as eluent gave 2.0 g of the title compound as an off white solid, m.p. 140-142° C. 1H NMR (DMSO-d6): δ 10.7 (s, 1H); 7.63 (d, 2H); 7.47 (d, 2H); 6.82 (t, 1H); 6.57 (d, 1H); 6.52 (d, 1H); 4.53 (m, 1H); 4.43 (dd, 1H); 4.34 (dd, 1H); 4.16 (dd, 1H); 4.10 (dd, 1H); 2.38 (s, 3H). MS (ESI) m/z359 ([M−H]−).

후처리

  1. washwashed with water (2×200 mL), saturated sodium bicarbonate (200 mL) saturated sodium chloride (200 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationFiltration, evaporation in vacuum and column chromatography on silica gel with 1% methanol/methylene chloride as eluent

출처 및 근거

ORD 기록
ord-d15d4f81679e47ef8362b2c741e9cd7b
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919334B2

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