Potassium Carbonate → (E)-methyl 2-[2-(6-chloro-3-[2-methylphenylthio]-1,2,4-triazin-5-yloxy)-phenyl]-3-methoxypropenoate

HRID 1585980Notes

Reaction equation

HRID 1585980 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:4][C:3]=1Cl.C(=O)([O-])[O-].[K+].[K+].[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1/[C:30](=[CH:35]\[O:36][CH3:37])/[C:31]([O:33][CH3:34])=[O:32].C1OCCOCCOCCOCCOCCOC1.[F-].[Cs+]>C(#N)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:4][C:3]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1/[C:30](=[CH:35]\[O:36][CH3:37])/[C:31]([O:33][CH3:34])=[O:32]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 2855718-Crown-6HCID 14326252Methyl (2E)-2-(2-hydroxyphenyl)-3-methoxyprop-2-enoateHCID 21217653Dichloro-(2-methylphenylthio)-1,2,4-triazine

Product 1

HCID 86754422(E)-methyl 2-[2-(6-chloro-3-[2-methylphenylthio]-1,2,4-triazin-5-yloxy)-phenyl]-3-methoxypropenoateYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a stirred solution of the dichloro-(2-methylphenylthio)-1,2,4-triazine formed in the reaction above (0.35 g) in dry acetonitrile (10 ml) was added dry potassium carbonate (0.18 g), followed by a solution of (E)-methyl 2-(2-hydroxyphenyl)-3-methoxypropenoate (0.27 g) in dry acetonitrile (2 ml), in one portion, at room temperature. A catalytic amount of 18-crown-6 and dry caesium fluoride (0.20 g) were then added. After stirring at room temperature for 11.5 hours, the mixture was diluted with acetonitrile (25 ml) and filtered through Hyflo Supercel filter aid. The filtrate was concentrated under reduced pressure and the residue was chromatographed twice using first ether-n-hexane (1:1) and then n-hexane-dichloromethane-acetonitrile (16:4:1) as eluent to afford (E)-methyl 2-[2-(6-chloro-3-[2-methylphenylthio]-1,2,4-triazin-5-yloxy)-phenyl]-3-methoxypropenoate as a pale yellow gum (0.16 g, 28%); IR max (nujol mull): 1710, 1630 cm-1 ; 1H NMR δ2.27(3H,s), 3.64(3H,s), 3.75(3H,s), 6.90-6.97(1H,m), 7.09-7.39(6H,m), 7.45-7.53(1H,m), 7.49(1H,s) ppm.

Workup

  1. filtrationfiltered through Hyflo Supercel
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was chromatographed twice

Sources & evidence

ORD record
ord-4910508cf901446d8127f89369cc955f
Source dataset
uspto-grants-1999_08
Patent number
US05942509

Reaction notes

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