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Sulfuric Acid → Pyrifluquinazon

HRID 1663296
Notes
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Reaction equation

HRID 1663296 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:23])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])=[CH:11][CH:12]=2)[CH2:7][N:6]([N:24]=[CH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:5]1=[O:32])(=[O:3])[CH3:2].S(=O)(=O)(O)O>[C].[Pd].CN(C)C=O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:23])([C:19]([F:20])([F:21])[F:22])[C:15]([F:17])([F:18])[F:16])=[CH:11][CH:12]=2)[CH2:7][N:6]([NH:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:5]1=[O:32])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 73031688HCID 73031688, compound

Product 1

HCID 11842644Pyrifluquinazon

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In a 200-ml autoclave were placed 9.25 g (20 mmol) of 1-acetyl-3,4-dihydro-3-(3-pyridylmethylideneamino)-6-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-2(1H)-quinazolinone, 0.21 g (0.05 mmol) of 5% palladium-carbon (containing 50% water), 0.4 g (98%, 4 mmol) of concentrated sulfuric acid and 50 ml of dimethylformamide. They were heated to 60° C. with stirring and the reaction was carried out at a hydrogen pressure of 2 kg/cm2 until the hydrogen absorption rate decreased. After the reaction mixture was cooled to room temperature, the catalyst was removed by filtration. The filtrate was analyzed by high performance liquid chromatography. The result is shown in Table 1 below.

Workup

  1. customthe reaction was carried out at a hydrogen pressure of 2 kg/cm2 until the hydrogen absorption rate
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customthe catalyst was removed by filtration

Sources & evidence

ORD record
ord-401e2c1d412c4d47ad588a5d44831f78
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08034931B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes