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Water → 1-(3,5-Dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}-2-diethylphosphonoethanone

HRID 990741
Notes
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Reaction equation

HRID 990741 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chlorideHCID 23665647Potassium tert-butoxideHCID 54149683Diethyl {2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}methylphosphonate

Product 1

HCID 536619561-(3,5-Dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}-2-diethylphosphonoethanone
Yield 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-3ecf0ca0a391428fbe6d8720619d4fd1
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06462049B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes