Sodium Hydroxide → HCID 178496237, compound

HRID 2167296Notes

Reaction equation

HRID 2167296 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:4][C:3]=1[C:16]1[NH:17][CH2:18][C:19]([CH3:25])([C:21]([O:23]C)=[O:22])[N:20]=1.[OH-].[Na+]>CO.O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:4][C:3]=1[C:16]1[NH:17][CH2:18][C:19]([CH3:25])([C:21]([OH:23])=[O:22])[N:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178496236HCID 178496236, compound

Product 1

HCID 178496237HCID 178496237, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4,5-dihydro-1H-imidazole-4-carboxylate (0.17 g, 0.5 mmol) in MeOH (5 mL) was added NaOH (40 mg, 1.0 mmol) and water (one drop). The resulting solution was stirred for 2 h at room temperature. The solvent was evaporated under vacuum and the residue was purified by Combi Flash to obtain the title compound as colorless oil (100 mg, 60%). 1H NMR (300 MHz, CD3OD, n=2): δ 7.65-7.85 (m, 1H), 6.55-6.75 (m, 2H), 4.30-4.40 (m, 1H), 4.10-4.30 (m, 2H), 3.70-3.95 (m, 2H), 3.65-3.70 (m, 2H), 3.55-3.65 (m, 2H), 3.33 (s, 3H), 1.74 (s, 3H). LC-MS (ES, m/z): 339 [M+H]+.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was purified by Combi Flash

Sources & evidence

ORD record
ord-1211d145abe348eea3e44fdcbc18a192
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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