HCID 14294199, compound → HCID 14294239, compound

HRID 2073368Notes

Reaction equation

HRID 2073368 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[N:10][C:9]=2[S:13]CCC(OCC)=O)=[CH:4][CH:3]=1.[O-]CC.[K+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][N:11]=[N:10][C:9]=2[SH:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14294199HCID 14294199, compoundHCID 23670592Potassium ethoxide

Product 1

HCID 14294239HCID 14294239, compoundYield 123.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 13.8 g of 3-[[5-(4-methylphenyl)1,2,3-thiadiazol-4-yl]thio]propanoic acid, ethyl ester in 250 ml of dry ethanol was treated with 200 ml of 1M potassium ethoxide in ethanol. After standing 1.5 hours, the solvent was removed in vacuo to about 100 ml and 400 ml of anhydrous ether was added. The solid was collected, washed with ether, dissolved in methanol and filtered. The filtrate was concentrated to a small volume and then diluted with 400 ml of anhydrous ether. The solid was collected and dried in vacuo, giving 11.5 g of 5-(4-methylphenyl)1,2,3-thiadiazole-4-thiol, monopotassium salt as a yellow solid, mp>125° C. (dec.).

Workup

  1. customthe solvent was removed in vacuo to about 100 ml and 400 ml of anhydrous ether
  2. additionwas added
  3. customThe solid was collected
  4. washwashed with ether
  5. dissolutiondissolved in methanol
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to a small volume
  8. additiondiluted with 400 ml of anhydrous ether
  9. customThe solid was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-0ab1c11bfc5b46b99123d216d7b11e88
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

Loading…