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Sodium Hydroxide → 2-(2-hydroxy-1-methylethyl)-1H-benzoimidazole-4-carboxylic acid

HRID 388812
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HRID 388812 반응식
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11].C[O:14][C:15](=O)[CH:16]([CH3:19])[CH2:17]O.[OH-].[Na+]>Cl>[OH:14][CH2:15][CH:16]([C:19]1[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([OH:2])=[O:12])[C:5]=2[N:11]=1)[CH3:17]
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 521128Methyl 3-hydroxy-2-methylpropanoateHCID 5718252,3-Diaminobenzoic acid methyl ester

생성물 1

HCID 668107842-(2-hydroxy-1-methylethyl)-1H-benzoimidazole-4-carboxylic acid수율 25.8%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
90 °C

실험 절차

To a solution of 2,3-diaminobenzoic acid methyl ester (2.1 g, 14.1 mmol) in 4 M HCl (90 mL) was added 2-methyl-3-hydroxypropionic acid methyl ester (5 g, 42.3 mmol). The mixture was stirred at ˜90° C. for 24 h. It was neutralized by use of aqueous sodium hydroxide solution to pH ˜3, and concentrated to dryness. The residue was suspended in methanol, and filtered through a filter paper. After the filtrate was concentrated, the remaining solid residue was dissolved in water and washed with ethyl acetate. The aqueous solution was evaporated in vacuo yielding the title intermediate as a pale yellow oil (˜800 mg). The crude product was used in the next step without further purification. (m/z): [M+H]+ calcd for C11H12N2O3 221.09. found 221.3. 1H-NMR (CD3OD) δ (ppm) 8.1 (d, 1H), 7.9 (m, 1H), 7.6 (t, 1H), 3.8 (m, 2H), 3.6 (m, 1H), 1.4 (d, 3H).

후처리

  1. concentrationconcentrated to dryness
  2. filtrationfiltered through a filter paper
  3. concentrationAfter the filtrate was concentrated
  4. dissolutionthe remaining solid residue was dissolved in water
  5. washwashed with ethyl acetate
  6. customThe aqueous solution was evaporated in vacuo

출처 및 근거

ORD 기록
ord-d4441f15395949ad923ccdc5adfd3cef
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377964B2

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