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

HRID 1585980
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HRID 1585980 반응식
[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]
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매3회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4910508cf901446d8127f89369cc955f
출처 데이터셋
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05942509

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