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Ammonium Chloride → 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole

HRID 971086
Notes
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Reaction equation

HRID 971086 reaction equation
Cl[CH:2]=[CH:3][C:4]1[C:5]([C:11]([F:14])([F:13])[F:12])=[N:6][N:7]([CH3:10])[C:8]=1[CH3:9].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1COCC1>[C:3]([C:4]1[C:5]([C:11]([F:13])([F:14])[F:12])=[N:6][N:7]([CH3:10])[C:8]=1[CH3:9])#[CH:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 851512404-(2-chloroethenyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 104424634-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazoleYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.27 g (5.67 mmol) of 4-(2-chloroethenyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole from Example 1 are dissolved in 40 ml of dry THF and placed under a protective gas atmosphere. After cooling the reaction solution to 0° C., 1.91 (17.0 mmol) of potassium tert-butoxide are introduced and, after the addition is complete, the mixture is stirred at 20° C. for 3 hours. After the end of the reaction, a saturated ammonium chloride solution (25 ml) is added and the mixture is extracted twice with 30 ml each time of methylene chloride. The combined organic phases are dried over magnesium sulphate, the solvent is removed by distillation and 4-ethynyl-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole is isolated as a microcrystalline solid in a yield of 79% of theory.

Workup

  1. additionafter the addition
  2. customAfter the end of the reaction
  3. extractionthe mixture is extracted twice with 30 ml each time of methylene chloride
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-39a38832c0b64342b84735591a9537eb
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07312350B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes