HCID 7576862, compound → 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid

HRID 1110961Notes

Reaction equation

HRID 1110961 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([O:9]CC1C=CC([N+]([O-])=O)=CC=1)=[O:8]>O1CCCC1.[Zn]>[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 7576862HCID 7576862, compound

Product 1

HCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 270 mg of 4-methyl-5-p-nitrobenzyloxycarbonyl-1,2,3-thiadiazole in 7 ml of tetrahydrofuran and 7 ml of 0.35M phoshate buffer (pH 6.1) was added 2.7 g of zinc powder, and the reaction mixture was stirred for 4 hours at room temperature. After the reaction, the reaction mixture was filtered using Celite and the filtrate was rendered alkaline by adding sodium carbonte and washed with ethyl acetate. The aqueous layer was then acidified by hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, the solvent was removed under reduced pressure. The resulting residue was purified using silica gel column chromatography to give 120 mg (91.0%) of 4-methyl-5-hydroxycarbonyl-1,2,3-thiadiazole. m.p. 190° C.

Workup

  1. customAfter the reaction
  2. filtrationthe reaction mixture was filtered
  3. additionby adding sodium carbonte
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting residue was purified

Sources & evidence

ORD record
ord-a5276d3953e849bfb22fd48dd3ec72ad
Source dataset
uspto-grants-1990_12
Patent number
US04977256

Reaction notes

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