Ammonium Chloride → HCID 86598134, compound

HRID 860620Notes

Reaction equation

HRID 860620 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.[Cl-].[NH4+]>C(OCC)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

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 69056995HCID 69056995, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86598134HCID 86598134, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 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 consumtion 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. stirringwith stirring
  2. extractionextracted
  3. customThe organic layer is collected
  4. washwashed with cold water (2×) and brine
  5. dry with materialThe solution is then dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-05ccaaadd6c149c4a2c6abdac637fae1
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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