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Acetone → Cyclopyrimorate

HRID 1039588
Notes
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Reaction equation

HRID 1039588 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[C:4]([OH:19])[CH:3]=1.CC(C)=O.C(=O)([O-])[O-].[K+].[K+].[N:30]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>O>[N:30]1([C:36]([O:19][C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=2[O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 848104-Morpholinecarbonyl chlorideHCID 178424441HCID 178424441, compound

Product 1

HCID 23013854CyclopyrimorateYield 99.2%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To 19.0 g (68.8 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol were added 51.3 g of acetone and 10.5 g (75.7 mmol) of potassium carbonate, and the resultant mixture was stirred at 30° C. To the mixture was added dropwise 11.3 g (75.7 mmol) of morpholinecarbonyl chloride over one hour. The reaction mixture was subjected to reaction at 30° C. for 5 hours. After completion of the reaction, pure water was added to the reaction mixture to deposit solids, and then the solids were taken out by filtration. The resultant solids were dried under a reduced pressure, and the solids were quantitatively determined by an HPLC internal standard analysis method, which showed that 26.6 g of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl morpholine-4-carboxylate (yield: 99%) was obtained.

Workup

  1. customThe reaction mixture was subjected to reaction at 30° C. for 5 hours
  2. additionwas added to the reaction mixture to deposit solids
  3. filtrationthe solids were taken out by filtration
  4. customThe resultant solids were dried under a reduced pressure

Sources & evidence

ORD record
ord-d2a752ee67d44c63b734f518873b4993
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552182B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes