4-(Diethylamino)benzaldehyde → HCID 178463809, compound

HRID 431717Notes

Reaction equation

HRID 431717 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 178463809HCID 178463809, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
145 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-468ef4aa63f642c78e6e003b0413293d
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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