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Toluene → HCID 17747836, compound

HRID 555955
Notes
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Reaction equation

HRID 555955 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([C:13]1[C:14]([CH3:20])=[N:15][N:16]([CH3:19])[C:17]=1[F:18])=[O:12])(=[O:3])[CH3:2].[CH2:21]([Mg]Cl)[CH:22](C)[CH3:23].[C:27]1(C)C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[F:18][C:17]1[N:16]([CH3:19])[N:15]=[C:14]([CH3:20])[C:13]=1[C:11]([NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:1]([OH:3])([CH3:27])[CH2:2][CH:22]([CH3:23])[CH3:21])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 12979270N-(2-acetylphenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideHCID 178418368HCID 178418368, compound

Product 1

HCID 17747836HCID 17747836, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-10 °C

Procedure

Under argon and with stirring at −10° C., N-(2-acetylphenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (as a solid, 10 g, 36.3 mmol) and isobutylmagnesium chloride (as a 2 M solution in THF, 41.7 ml; 83.55 mmol) are added simultaneously and continuously to 400 ml of toluene over a period of 150 minutes. The mixture is allowed to warm to room temperature, 200 ml of ammonium chloride solution are added, the mixture is extracted three times with in each case 100 ml of ethyl acetate and the organic phases are dried using sodium sulphate and concentrated under reduced pressure. This gives 5-fluoro-N-[2-(1-hydroxy-1,3-dimethylbutyl)phenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamide (14.2 g, purity (GC/MS) 72.8%; 85% of theory) which still contains 14% of starting material.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe mixture is extracted three times with in each case 100 ml of ethyl acetate
  3. customthe organic phases are dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-897fadea5e0d4a708ea81576f4d35820
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053572B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes