Sodium → 5-(alpha-Carboxy-m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid

HRID 1395201Notes

Reaction equation

HRID 1395201 reaction equation
[Na].C[O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][N:7]=1)=[O:5].Br[CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[C:15]([O:17]C)=[O:16]>CO>[C:15]([CH:14]([S:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([OH:3])=[O:5])=[N:7][CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:28])[F:27])[CH:20]=1)([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 127827695-Mercaptopyridine-2-carboxylic acid methyl esterHCID 19796654Methyl 2-bromo-2-[3-(trifluoromethyl)phenyl]acetate

Product 1

HCID 538880015-(alpha-Carboxy-m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the solution prepared from 80 ml of methanol and 0.89 g of sodium, 6.53 g of 5-mercaptopyridine-2-carboxylic acid methyl ester are added, followed by the solution of 12.6 g of methyl α-bromo-m-trifluoromethylphenylacetate in 50 ml of methanol while stirring under nitrogen. The mixture is warmed for 1/2 hour on the steam bath and allowed to stand at room temperature overnight. It is evaporated, the residue taken up in water-diethyl ether, the organic phase washed with water, dried and evaporated. The residue is dissolved in the minimum amount of methanolisopropanol (1:1), the solution mixed with 85 ml of N aqueous sodium hydroxide, warmed for 1/2 hour on the steam bath, and stored at room temperature overnight. The mixture is evaporated, the residue taken up in 2 N hydrochloric acid and the mixture extracted with diethyl ether-ethyl acetate (1:1). The extract is washed with water, dried and evaporated and the residue recrystallized from diethyl ether-ethyl acetate, to yield the 5-(α-carboxy-m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid melting at 190°-195°.

Workup

  1. additionare added
  2. temperatureThe mixture is warmed for 1/2 hour on the steam bath
  3. customIt is evaporated
  4. washthe organic phase washed with water
  5. customdried
  6. customevaporated
  7. dissolutionThe residue is dissolved in the minimum amount of methanolisopropanol (1:1)
  8. additionthe solution mixed with 85 ml of N aqueous sodium hydroxide
  9. temperaturewarmed for 1/2 hour on the steam bath
  10. waitstored at room temperature overnight
  11. customThe mixture is evaporated
  12. extractionthe mixture extracted with diethyl ether-ethyl acetate (1:1)
  13. washThe extract is washed with water
  14. customdried
  15. customevaporated
  16. customthe residue recrystallized from diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-039e7d7b5aa443d7812beb5804d24ec4
Source dataset
uspto-grants-1980_05
Patent number
US04202901

Reaction notes

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