Ethanol → HCID 178477525, compound

HRID 2301877Notes

Reaction equation

HRID 2301877 reaction equation
[K].[CH2:2]([O:4][C:5]([C:7]1[O:11][C:10](=[S:12])[NH:9][N:8]=1)=[O:6])C.IC.[CH3:15][CH2:16]O>>[CH2:15]([SH:12]=[C:10]1[NH:9][N:8]=[C:7]([C:5]([O:4][CH3:2])=[O:6])[O:11]1)[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 6328Methyl iodideHCID 88082025HCID 88082025, compound

Product 1

HCID 178477525HCID 178477525, compoundYield 50%

Procedure

Following the procedure of Partyka and Crenshaw in U.S. Pat. No. 4,001,238, a solution of ethyl-1,3,4-oxadiazole-2-thione-5-carboxylate potassium salt dimethylsulfoxide solvate (4.1 g, 24 mmol) and iodomethane (6.7 g, 47 mmol) are heated for 1 hour at reflux in EtOH (20 mL). A solid is removed by vacuum filtration, and the filtrate is concentrated. Water (40 mL) is added to the resultant material, a solid is isolated by vacuum filtration, dried at 50° C./0.5 mmHg overnight to afford the desired product (2.3 g, 50%).

Workup

  1. temperatureare heated for 1 hour
  2. customA solid is removed by vacuum filtration
  3. concentrationthe filtrate is concentrated
  4. additionWater (40 mL) is added to the resultant material
  5. customa solid is isolated by vacuum filtration
  6. customdried at 50° C./0.5 mmHg overnight

Sources & evidence

ORD record
ord-8e73108558ab448d8225397b1c99ee68
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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