4-(Diethylamino)benzaldehyde → HCID 178463809, 화합물

HRID 431717

반응식

HRID 431717 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([N:15]([CH2:24][CH3:25])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[CH3:14]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:13]([N:15]([C:16]1[CH:17]=[CH:18][C:19]([C:20]2[NH:12][C:11]3[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=3[N:1]=2)=[CH:22][CH:23]=1)[CH2:24][CH3:25])[CH3:14]

참가 물질

4

반응물 2

HCID 671144-(Diethylamino)benzaldehydeHCID 1355243,5-Diamino-2-methylbenzoic acid

생성물 1

HCID 178463809HCID 178463809, 화합물수율 82%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

반응 조건

온도
145 °C

실험 절차

Methyl 3,4-diaminobenzoate (0.73 g, 4.42 mmol), 4-(diethylamino)benzaldehyde (3.0 g, 16.9 mmol) were dissolved in nitrobenzene (30 mL) and refluxed on a 145° C. oil bath overnight. The nitrobenzene was then removed in vacuo using a Kugelrohr apparatus (60° C., 0.1 mm Hg). The remaining oily residue was dissolved in CHCl3 and washed with water (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The crude oil was then purified through colurnn chromatography using a solvent system of 1% MeOH/CHCl3 to give methyl 2-(4-(N,N-diethyl)aminophenyl)benzimidazole-6-carboxylate as a yellowish solid (1.17 g, 82% yield). TLC (2.5% MeOH/CHCl3) Rf=0.26; 1H-NMR (500 MHz, CDCl3) 9.87 (s br, 1H), 8.30 (s br, 1H), 7.94 (dd, 1.5, 8.5, 1H), 7.91 (d, 8.5, 2H), 7.60 (s br, 1H), 6.72 (d, 8.5, 2H), 3.42 (q, 7.0, 4H), 1.21 (t, 7.0, 6H); IR (neat) 3508, 2063, 2920, 1712, 1611, 1504, 1434, 1360, 1307, 1269, 1205, 1157, 1082, 1008, 821, 751.

후처리

  1. customThe nitrobenzene was then removed in vacuo
  2. customa Kugelrohr apparatus (60° C., 0.1 mm Hg)
  3. dissolutionThe remaining oily residue was dissolved in CHCl3
  4. washwashed with water (3×50 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was then purified through colurnn chromatography

출처 및 근거

ORD 기록
ord-468ef4aa63f642c78e6e003b0413293d
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660742B2

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