Dimethylformamide → HCID 118001333, compound

HRID 628538Notes

Reaction equation

HRID 628538 reaction equation
P(Cl)(Cl)([Cl:3])=O.[OH:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=2)[CH:8]=1.[CH3:24][N:25]([CH3:28])[CH:26]=[O:27]>>[Cl:3][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=2)[C:8]=1[CH:26]=[O:27].[CH3:23][C:15]1[CH:14]=[C:13]([C:9]2[C:8]([CH:7]=[O:6])=[C:28]([Cl:3])[N:25]([CH3:24])[N:10]=2)[CH:18]=[CH:17][C:16]=1[OH:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178422872HCID 178422872, compound

Product 2

HCID 118001333HCID 118001333, compoundHCID 136941910HCID 136941910, compound

Procedure

At 0° C., to phosphorus oxychloride 43 g was added N,N-dimethylformamide 3.2 g and the resulting mixture was stirred for a half hour. Thereto was added 5-hydroxy-3-(4-isopropoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole (described in Reference preparation example 95) 8.3 g. The resulting mixture was stirred at 100° C. for ten hours and the reaction solvent was distilled off under reduced pressure. To the reaction mixture was added ice water 100 ml and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and were dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 5-chloro-4-formyl-3-(4-isopropoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 5.1 g and 2-methyl-4-(5-chloro-4-formyl-1-methyl-1H-pyrazol-3-yl)-phenol 0.6 g.

Workup

  1. stirringThe resulting mixture was stirred at 100° C. for ten hours
  2. distillationthe reaction solvent was distilled off under reduced pressure
  3. additionTo the reaction mixture was added ice water 100 ml
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-51078a089fb44aa9a495df9a5a63a464
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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