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Toluene → Ethyl 3-difluoromethyl-1-methyl-4-pyrazole carboxylate

HRID 1045038
Notes
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Reaction equation

HRID 1045038 reaction equation
[C:1]1(C)C=CC=CC=1.[F:8][CH:9]([F:20])[C:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][NH:12][N:11]=1.[OH-].[Na+].S(OC)(OC)(=O)=O>[Cl-].C[N+](C)(C)C.O>[F:20][CH:9]([F:8])[C:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]([CH3:1])[N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 178469922HCID 178469922, compound

Product 1

HCID 11644126Ethyl 3-difluoromethyl-1-methyl-4-pyrazole carboxylate

Reagents, catalysts & solvents 2

HCID 6379
Tetramethylammonium chloride
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

The toluene solution of crude ethyl 3-difluoromethylpyrazole-4-carboxylate was stirred and cooled to 20° C. Water (260 ml), tetramethylammonium chloride (10% aqueous solution, 15.0 g), and 25% NaOH solution (36-60 g) were added in sequence. Dimethyl sulphate (99.5%, 94.5 g, 0.75 mol) and additional 25% NaOH were fed simultaneously over 2 hours at 20° C. while maintaining the pH between 10.5 and 12.0. After 2 hours post reaction, the bottom aqueous phase was separated off.

Workup

  1. temperaturewhile maintaining the pH between 10.5 and 12.0
  2. customAfter 2 hours post reaction
  3. customthe bottom aqueous phase was separated off

Sources & evidence

ORD record
ord-c02fbd31e5b14b1c942e53f7a6342776
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563747B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes