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

HRID 1710029

Reaction equation

HRID 1710029 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d55efcf035df427ab8651259db9fc160
Source dataset
uspto-grants-1990_08
Patent number
US04952570

Linked notes

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