Ethylene Glycol → HCID 22615139, compound

HRID 842649Notes

Reaction equation

HRID 842649 reaction equation
[C:1]([C:4]1[C:5]([F:13])=[C:6](N)[C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:14][C:15](C1C=CC(OC)=CC=1F)=[O:16].C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:13][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:1]1([CH3:2])[O:16][CH2:15][CH2:14][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 5928212'-Fluoro-4'-methoxyacetophenoneHCID 22615118HCID 22615118, compound

Product 1

HCID 22615139HCID 22615139, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Starting material 3-acetyl-2-fluoro-6-methoxyphenyl-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-methoxyphenyl)-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 (q, 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-fcffd4632e2a4e369ccb906ba477ab68
Source dataset
uspto-grants-2002_04
Patent number
US06376492B1

Reaction notes

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