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Thioglycolic Acid → Diclazuril

HRID 355362
ノート
印刷プレビュー

反応式

HRID 355362 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[C:21](C(O)=O)=[N:20]2)[CH:5]=[C:6]([Cl:18])[C:7]=1[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:9]#[N:10].SCC(O)=O.C(=O)([O-])O.[Na+]>O>[Cl:18][C:6]1[CH:5]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:9]#[N:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1133Thioglycolic AcidHCID 516892Sodium BicarbonateHCID 189421702-(3,5-Dichloro-4-((RS)-(4-chlorophenyl)cyanomethyl)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid2 回

生成物 1

HCID 456389Diclazuril

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
180 °C

実験手順

A mixture of 11.1 parts of 2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid (intermediate 5) and 15 parts of 2-mercaptoacetic acid is stirred and heated for 2 hours at 180 degrees C. The reaction mixture is cooled, water is added and the whole is treated with sodium hydrogen carbonate. The product is extracted with trichloromethane. The organic layer is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo. The residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitrile.

後処理

  1. temperatureThe reaction mixture is cooled
  2. extractionThe product is extracted with trichloromethane
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated in vacuo
  10. stirringThe residue is stirred in 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customdried

出典と根拠

ORDレコード
ord-5f21db4a99db4055ae42fdfb71a73b13
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05830893

反応ノート

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