Ethylene Glycol → HCID 15617190, compound

HRID 2351624Notes

Reaction equation

HRID 2351624 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C(O)CO>O>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[N:13]=[C:14]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 14390501HCID 14390501, compound

Product 1

HCID 15617190HCID 15617190, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[3-[[3-(trifluoromethyl)benzoyl]amino]-2-pyridinyl]glycine ethyl ester (22.0 g, 0.06 mole) and ethylene glycol (100 ml) was heated at reflux for 40 minutes. The reaction mixture was poured into water (300 ml) and cooled. The solid was collected by filtration, washed with water (200 ml), and dried. The solid was recrystallized from isopropyl ether-tetrahydrofuran to give in 2 crops 18.4 g (0.053 mole) of crude 2-(3-trifluoromethylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester. This solid together with potassium hydroxide pellets (4.7 g, 0.084 mole), 95% ethanol (150 ml), and water (10 ml) was refluxed for 21/2 hrs. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (100 ml) and extracted with methylene chloride (2×30 ml). The aqueous portion was acidified with glacial acetic acid and filtered after precipitation was complete. The filter cake was suspended in water (200 ml) and filtered. Recrystallization from tetrahydrofuran-isopropyl ether gave 15.3 g (91%). A 1.6-g sample was recrystallized from tetrahydrofuran-isopropyl ether to give 1.0 g of an off-white solid, mp 240°-241.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 minutes
  3. temperaturecooled
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (200 ml)
  6. customdried
  7. customThe solid was recrystallized from isopropyl ether-tetrahydrofuran

Sources & evidence

ORD record
ord-1b001d7ed10e42acbc4e290e62eb86a2
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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