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Trityl chloride → methyl 1-trityl-1H-imidazole-4-carboxylate

HRID 720638
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HRID 720638 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][NH:8][CH:9]=1)=[O:4].C(N(CC)CC)C.[C:17]1([C:23](Cl)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:9]=1)=[O:4]
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참가 물질

5

반응물 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418785HCID 178418785, 화합물

생성물 1

HCID 10429115methyl 1-trityl-1H-imidazole-4-carboxylate수율 98.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

A solution of 1H-Imidazole-4-carboxylic acid methyl ester (1.0 g, 7.93 mmol) in N,N-dimethylformamide at 25° C. was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 mmol). The reaction was stirred at 25° C. for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50:50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.88 g, 98.6%) as a white foam: 1H NMR (DMSO-d6, 300 MHz) δ7.56 (s, 1H), 7.47 (m, 10H), 7.09 (m, 6H), 3.69 (s, 3H).

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4929b37ac1044b4fb3ad52b70cff5b3a
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07135475B2

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