HCID 68758033, compound → HCID 67960495, compound

HRID 707658Notes

Reaction equation

HRID 707658 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:8][N:7]=1)=O)C.[CH3:17][Mg]I>C1COCC1>[O:3]=[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:8][N:7]=1)[CH3:17]

Participants

4

Reactant 2

HCID 68758033HCID 68758033, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 67960495HCID 67960495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a mixture of 2-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)-pyridine (2 gm) in THF (40 ml) was added methyl magnesium iodide (15 ml, 1.4 M solution in THF) at −40° C. over a period of 15 minutes. The reaction mixture was stirred for 2 h at −40° C. It was quenched by addition of aqueous ammonium chloride solution (20 gm) and stirred at 0° C. over a period of 10 minutes. It was extracted with ethyl acetate (100 ml×2). Combined organic layers was washed with water and evaporated under vacuum to provide a title compound in 1.5 gm quantity (86%) as off white solid.

Workup

  1. customIt was quenched by addition of aqueous ammonium chloride solution (20 gm)
  2. stirringstirred at 0° C. over a period of 10 minutes
  3. extractionIt was extracted with ethyl acetate (100 ml×2)
  4. washCombined organic layers was washed with water
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-7ed8d54cadcd4914ae47bfd07aa39ffb
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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