Diethyl Ether → Ethanone, 1-(4-methyl-1,2,3-thiadiazol-5-yl)- (9CI)

HRID 396537Notes

Reaction equation

HRID 396537 reaction equation
CON(C)[C:4]([C:6]1[S:10][N:9]=[N:8][C:7]=1[CH3:11])=[O:5].[CH2:13](OCC)C.C[Mg]I>C1COCC1>[C:4]([C:6]1[S:10][N:9]=[N:8][C:7]=1[CH3:11])(=[O:5])[CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23003463HCID 23003463, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 23003518Ethanone, 1-(4-methyl-1,2,3-thiadiazol-5-yl)- (9CI)Yield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-4-methyl-1,2,3-thiadiazole-5-carboxamide (11.31 g, 60.4 mmol) in THF (100 ml) was added 2M diethyl ether solution of methylmagnesium iodide (45.3 ml, 90.6 mmol) over 0.5 h at 0° C. The mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous ammonium chloride (100 ml) and then extracted with diethyl ether (200 ml×2). The extracts were dried (MgSO4) and concentrated to give 7.49 g (87%) of the title compound as a pale brown oil.

Workup

  1. customThe mixture was quenched with saturated aqueous ammonium chloride (100 ml)
  2. extractionextracted with diethyl ether (200 ml×2)
  3. dry with materialThe extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c8839183b754a71ad88b973b7d40d88
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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