3-[[5-[4-(1,1-Dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]propanoic acid, ethyl ester → HCID 14294241, compound

HRID 1381712Notes

Reaction equation

HRID 1381712 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][N:14]=[N:13][C:12]=2[S:16]CCC(OCC)=O)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[O-]CC.[K+]>C(O)C>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:15][N:14]=[N:13][C:12]=2[SH:16])=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 142942003-[[5-[4-(1,1-Dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]propanoic acid, ethyl esterHCID 23670592Potassium ethoxide

Product 1

HCID 14294241HCID 14294241, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 15.9 g of 3-[[5-[4-(1,1-dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]propanoic acid, ethyl ester in 75 ml of anhydrous ethanol was treated with 105 ml of 0.5M potassium ethoxide in ethanol. After 3 hours the solvent was partially removed in vacuo and 200 ml of anhydrous ether was added. The resulting solid was collected, washed with ether, redissolved in methanol, filtered and the filtrate concentrated to 10-15 ml. A 250 ml portion of anhydrous ether was added and the solid was collected and dried in vacuo, giving 13 g of 5-[4-(1,1-dimethylethyl)phenyl]-1,2,3-thiadiazol-4-thiol, potassium salt as a yellow solid, mp >150° C.

Workup

  1. customAfter 3 hours the solvent was partially removed in vacuo and 200 ml of anhydrous ether
  2. additionwas added
  3. customThe resulting solid was collected
  4. washwashed with ether
  5. dissolutionredissolved in methanol
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated to 10-15 ml
  8. additionA 250 ml portion of anhydrous ether was added
  9. customthe solid was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-a3eaf5db50344522bd88863aa2ba9ffb
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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