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N-Hydroxypropionimidamide → 1-Chloro-5-(3,3-dichloroprop-2-enyloxy)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

HRID 497048
Notes
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Reaction equation

HRID 497048 reaction equation
[Cl:1][C:2]1[C:3]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)=[C:4]([CH:9]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([Cl:17])[Cl:16])[CH:11]=1)[C:5](OC)=[O:6].[C:33](=[N:37]O)([NH2:36])[CH2:34][CH3:35].[Na]>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([Cl:17])[Cl:16])[CH:9]=[C:4]([C:5]2[O:6][N:37]=[C:33]([CH2:34][CH3:35])[N:36]=2)[C:3]=1[O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][N:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4092053N-HydroxypropionimidamideHCID 5360545SodiumHCID 22318619Methyl 3-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzoate

Product 1

HCID 223186131-Chloro-5-(3,3-dichloroprop-2-enyloxy)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent
2×

Conditions

Temperature
40 °C

Procedure

0.05 g of methyl 3-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzoate and 0.028 g of propionamidoxime were dissolved in 1 ml of anhydrous ethanol. A solution of 0.008 g of sodium in 0.5 ml of ethanol was added to this solution. The mixture was stirred at 40° C. for 2 hours and at room temperature for 20 hours. The mixture was then concentrated, and diethyl ether and water were added. After shaking, the ether phase was isolated, dried and concentrated under reduced pressure, and the crude product was purified chromatographically. Yield: 0.017 g (32%)

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondiethyl ether and water were added
  3. stirringAfter shaking
  4. customthe ether phase was isolated
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customthe crude product was purified chromatographically

Sources & evidence

ORD record
ord-68ae83fbb67c491bb414b7c859e79a24
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06949551B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes