Ammonium Chloride → 1-[2-(1H-Imidazol-1-yl)-4-thiazolyl]ethanone

HRID 1170505Notes

Reaction equation

HRID 1170505 reaction equation
[CH3:1][Mg]Cl.CON(C)[C:7]([C:9]1[N:10]=[C:11]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[S:12][CH:13]=1)=[O:8].[NH4+].[Cl-]>C1COCC1>[N:14]1([C:11]2[S:12][CH:13]=[C:9]([C:7](=[O:8])[CH3:1])[N:10]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58654364HCID 58654364, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 586543761-[2-(1H-Imidazol-1-yl)-4-thiazolyl]ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl magnesium(II)chloride (1.12 mL of a 3.0 M solution in THF, 3.36 mmol) was added dropwise to a 0° C. solution of 2-imidazol-1-yl-thiazole-4-carboxylic acid methoxy-methyl-amide obtained from Step 1 (400 mg, 1.68 mmol) in THF (5 mL) under a nitrogen atmosphere. The reaction was then warmed to r.t. over a period of 2 hours, sat. NH4Cl (50 mL) was added and the solution was extracted with methylene chloride (2×70 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent gave 319 mg (98%) of 1-(2-imidazol-1-yl-thiazol-4-yl)-ethanone as a white solid which was which was used without further purification in the subsequent step. [M+H]+ 194.06.

Workup

  1. extractionthe solution was extracted with methylene chloride (2×70 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3d01d9e136614c0a9daaeb1b0dc77d53
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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