Lithium Hydroxide → HCID 23290176, compound

HRID 366854Notes

Reaction equation

HRID 366854 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[C:13]4[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Li+]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:13]4[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 9906491HCID 9906491, compound

Product 1

HCID 23290176HCID 23290176, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4 g (11.4 mmol) of ethyl 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-butanoate in 40 mL of THF was treated with 40 mL (80 mmol) of lithium hydroxide (2M in water), and the reaction was stirred at rt overnight. The mixture was washed with ether to remove non-acidic impurity. The aqueous layer was acidified with 3 N hydrochloric acid (HCl), and the solid was collected by filtration and dried in vacuo to give 2.77 g (75%) of 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-butanoic acid as an off-white solid: mp 177.0-179.8° C.; 1H NMR (DMSO, d6) δ 1.90 (quintet, J=7.3 Hz, 2H), 2.19 (t, J=6.9 Hz, 2H), 4.30 (t, J=7.7 Hz, 2H), 6.14 (s, 2H), 7.10 (d, J=8.1 Hz, 1H), 7.20-7.34 (m, 4H), 7.65 (dd, J=7.9, 1.2 Hz, 2H), 12.15 (br s, 1H); HRMS (EI) Calc'd for M+ : 325.1188, found: 325.1188. Anal. Calc'd for [C18H16N2O4 +0.43 CH2Cl2 ]: C, 61.39; H, 4.71; N, 7.77. Found: C, 61.39; H, 4.55; N, 7.79.

Workup

  1. washThe mixture was washed with ether
  2. customto remove non-acidic impurity
  3. filtrationthe solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5a056db7df2f4ed592bf1982d364b611
Source dataset
uspto-grants-2000_10
Patent number
US06130333

Reaction notes

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