Ethylene Glycol → HCID 22615139, compound

HRID 1457846Notes

Reaction equation

HRID 1457846 reaction equation
[C:1]([C:4]1[C:5]([F:16])=[C:6](N)[C:7]([O:13][CH3:14])=[CH:8][C:9]=1OCC)(=[O:3])[CH3:2].[CH3:17][C:18](C1C=CC(OC)=CC=1F)=[O:19].C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:16][C:5]1[CH:6]=[C:7]([O:13][CH3:14])[CH:8]=[CH:9][C:4]=1[C:1]1([CH3:2])[O:3][CH2:17][CH2:18][O:19]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 5928212'-Fluoro-4'-methoxyacetophenoneHCID 86585862HCID 86585862, compound

Product 1

HCID 22615139HCID 22615139, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Starting material 3-acetyl-2-fluoro-6-methoxyphenetyl-amine, was prepared in following manner: A mixture of 2-Fluoro-4-methoxyacetophenone (5 g) (Fluorochem), ethylene glycol (4 ml), and p-toluensulfonic acid (50 mg) in toluene was refluxed 10 hours to give 5.7 g of 2-(2-fluoro-4-methoxyphenyl)-2-methyl-1,3-dioxolane. This was converted to 2-fluoro-6-methoxy-3-(2-methyl-1,3-dioxol-2-yl)-benzaldehyde according to Example 362 of WO 93/03022. This compound was converted to 2-fluoro-6-methoxy-3-(2-methyl-1,3-dioxol-2-yl)-cinnamic acid ethylester according to the methods described in Example 353 of WO 93/03022. 2-Fluoro-6-methoxy-3-(2-methyl-1,3-dioxol-2-yl)cinnamic acid ethylester was then treated with KOH in dioxane and water to yield 2-fluoro-6-methoxy-3-(2-methyl-1,3-dioxol-2-yl)cinnamic acid. Hydrolysis with aqueous HCl in dioxane gave 3-acetyl-2-fluoro-6-methoxycinnamic acid. N-(3-Acetyl-2-fluoro-6-methoxyphenetyl)-N'-(5-chloropyrid-2-yl)-urea was then prepared in a manner analogous to the method in Example 7. 1H NMR (250 MHz, CDCl3) δ 9.18 (br s, 1H), 8.97 (br s, 1H), 7.85 (d, 1H), 7.83 (t, 1H), 7.51 (dd, 1H), 6.83 (d, 1H), 6.70 (d, 1H), 3.82 (s, 3H), 3.57 (g, 2H), 3.08-2.92 (m, 2H), 2.51 (d, 3H).

Workup

  1. customwas prepared
  2. temperaturewas refluxed 10 hours

Sources & evidence

ORD record
ord-006ee33455f84a888941e7a45b36d437
Source dataset
uspto-grants-1998_12
Patent number
US05849769

Reaction notes

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