O-Methylhydroxylamine hydrochloride → HCID 86598134, compound

HRID 490742Notes

Reaction equation

HRID 490742 reaction equation
CO[C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH:20]([CH3:22])[CH3:21])=[O:4].Cl.[CH3:24][O:25][NH2:26].[CH:27]([Mg]Cl)(C)C>O1CCCC1>[CH3:24][O:25][N:26]([CH3:27])[C:3]([C:5]1[S:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:14][CH:15]=2)=[N:7][C:6]=1[CH:20]([CH3:22])[CH3:21])=[O:4]

Participants

5

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69056995HCID 69056995, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86598134HCID 86598134, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid methyl ester (14 g, 40.1 mmol) is dissolved into anhydrous tetrahydrofuran (THF) (200 mL) and then cooled to −30° C. while stirring under nitrogen. N-methyl, N-methoxy amine hydrochloride (0.881 g, 9.04 mmol) is then added to the solution in one portion. Isopropyl magnesium chloride (8.73 mL, 2M soln. in THF, 17.46 mmol) is slowly added to the cooled suspension over 1 h. TLC will show complete consumption of starting material, then 30% solution of ammonium chloride is added with stirring. The reaction is diluted with diethyl ether and extracted. The organic layer is collected and washed with cold water (2×) and brine. The solution is then dried over anhydrous sodium sulfate, filtered, and concentrated. The 4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid methoxy-methyl-amide (0.705 g, 1.97 mmol) is obtained in pure form after flash column chromatography.

Workup

  1. customconsumption of starting material
  2. addition30% solution of ammonium chloride is added
  3. stirringwith stirring
  4. additionThe reaction is diluted with diethyl ether
  5. extractionextracted
  6. customThe organic layer is collected
  7. washwashed with cold water (2×) and brine
  8. dry with materialThe solution is then dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-090b097f2d2f4e739c0f517a08babbdd
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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