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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
ノート
印刷プレビュー

反応式

HRID 1585980 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒3 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4910508cf901446d8127f89369cc955f
出典データセット
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05942509

反応ノート

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