Thioglycolic Acid → HCID 13770337, compound

HRID 1249369Notes

Reaction equation

HRID 1249369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[C:22](C(O)=O)=[N:21]2)[CH:5]=[C:6]([CH3:19])[C:7]=1[C:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)([C:10]#[N:11])[CH3:9].SCC(O)=O.C(=O)([O-])O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]2)[CH:5]=[C:6]([CH3:19])[C:7]=1[C:8]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)([CH3:9])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 516892Sodium BicarbonateHCID 13770336HCID 13770336, compound

Product 1

HCID 13770337HCID 13770337, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 11.1 parts of 2-[3-chloro-4-[1-(4-chlorophenyl)-1-cyanoethyl]-5-methylphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid and 15 parts of 2-mercaptoacetic acid was stirred and heated for 2 hours at 180° C. The reaction mixture was cooled, water was added and the whole was treated with sodium hydrogen carbonate. The product was extracted with trichloromethane. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated in vacuo. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding 5 parts (50%) of 2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-α,6-dimethylbenzeneacetonitrile; mp. 226.7° C. (compound 1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with trichloromethane
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was 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 were collected
  9. customthe eluent was evaporated in vacuo
  10. stirringThe residue was stirred in 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-997c31912f7845598b34f6fe2cd6c707
Source dataset
uspto-grants-1986_12
Patent number
US04631278

Reaction notes

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