Thioglycolic Acid → alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-3-methoxybenzeneacetonitrile

HRID 1710029

반응식

HRID 1710029 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]#[N:29])[C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])[C:17](C(O)=O)=[N:16]3)=[CH:11][C:10]=2OC)=[CH:4][CH:3]=1.SC[C:32](O)=[O:33]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])[CH:17]=[N:16]3)=[C:13]([O:33][CH3:32])[CH:14]=2)[C:28]#[N:29])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 1133Thioglycolic AcidHCID 230351952-[4-[(4-Chlorophenyl)cyanomethyl]3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid

생성물 1

HCID 23035191alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-3-methoxybenzeneacetonitrile

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
175 °C

실험 절차

A mixture of 4.2 parts of 2-[4-[(4-chlorophenyl)cyanomethyl]3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid and 13 parts of 2-mercaptoacetic acid is stirred and heated for 2 hours at 175° C. After cooling, 150 parts of water are added. The aqueous phase is decanted and the remaining oil is stirred in water. The whole is treated with sodium hydrogen carbonate. The product is extracted with a mixture of trichloromethane and methanol (90:10 by volume). The extract is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo. The residue is crystallized from 8 parts of acetonitrile. The product is filtered off, washed with 2,2'-oxybispropane and dried, yielding α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-3-methoxybenzeneacetonitrile (intermediate 2).

후처리

  1. temperatureAfter cooling
  2. customThe aqueous phase is decanted
  3. stirringthe remaining oil is stirred in water
  4. additionThe whole is treated with sodium hydrogen carbonate
  5. extractionThe product is extracted with a mixture of trichloromethane and methanol (90:10 by volume)
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated in vacuo
  13. customThe residue is crystallized from 8 parts of acetonitrile
  14. filtrationThe product is filtered off
  15. washwashed with 2,2'-oxybispropane
  16. customdried

출처 및 근거

ORD 기록
ord-d55efcf035df427ab8651259db9fc160
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04952570

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