Dimethylformamide → HCID 86668974, compound

HRID 242184Notes

Reaction equation

HRID 242184 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23]([C:24]3[C:25]([CH3:30])=[N:26][O:27][C:28]=3[CH3:29])=[CH:22][C:21]([CH2:31][CH2:32][CH3:33])=[N:20]2)=[CH:15][CH:14]=1.C(Cl)Cl>C1(C)C=CC=CC=1.O>[CH3:30][C:25]1[C:24]([C:23]2[N:19]([C:16]3[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=3)[N:20]=[C:21]([CH2:31][CH2:32][CH3:33])[C:22]=2[CH:8]=[O:9])=[C:28]([CH3:29])[O:27][N:26]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 67120034HCID 67120034, compound

Product 1

HCID 86668974HCID 86668974, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
150 °C

Procedure

Phosphorus oxychloride (599 μL, 6.42 mmol) was added dropwise to dry N,N-dimethylformamide, (497 μL, 6.42 mmol) in toluene (0.6 mL) at 0° C. The mixture was stirred for 5 minutes. Then 4-(1-(4-methoxyphenyl)-3-propyl-1H-pyrazol-5-yl)-3,5-dimethylisoxazole (160 mg, 0.51 mmol) was added, dissolved in toluene (0.5 mL) and the reaction mixture was heated at 150° C. for 20 minutes in the microwave. CH2Cl2 and water were added, a phase separator was used to separate and dry the organic phase. Filtration through a short silica plug gave semi-crude 5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole-4-carbaldehyde which was used as such in the next step without further purification.

Workup

  1. customto separate
  2. customdry the organic phase
  3. filtrationFiltration through a short silica plug

Sources & evidence

ORD record
ord-9a189cd5ddbb47fd86732b177902b458
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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