Water → HCID 53661956, compound

HRID 230096Notes

Reaction equation

HRID 230096 reaction equation
[Cl:1][C:2]1[C:6]([C:7](Cl)=[O:8])=[C:5]([Cl:10])[N:4]([CH3:11])[N:3]=1.[CH3:12][C:13]1([C:19]2[S:20][CH:21]=[C:22]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[N:23]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CC(C)([O-])C.[K+].O>O1CCCC1>[Cl:1][C:2]1[C:6]([C:7](=[O:8])[CH:24]([C:22]2[N:23]=[C:19]([C:13]3([CH3:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[S:20][CH:21]=2)[P:25]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:32])=[C:5]([Cl:10])[N:4]([CH3:11])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chlorideHCID 23665647Potassium tert-butoxideHCID 54149683HCID 54149683, compound

Product 1

HCID 53661956HCID 53661956, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.85 g (4 mmols) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride and 1.32 g (4 mmols) of diethyl {2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}methylphosphonate were dissolved in 15 ml of dry tetrahydrofuran, and 1.12 g (10 mmols) of potassium t-butoxide was added thereto at room temperature. The reaction mixture was stirred for 1 hour at room temperature, and 20 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified through silica gel column chromatography to obtain 0.4 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}-2-diethylphosphonoethanone.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-cf74af0a353540adaf6d0dec069a3c5b
Source dataset
uspto-grants-2009_07
Patent number
US07566683B2

Reaction notes

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