Water → HCID 86741958, compound

HRID 2413455Notes

Reaction equation

HRID 2413455 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[CH:13]=[N:14][OH:15].[CH:16]1([N:22]=[C:23]=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O>CN(C)C=O>[CH:16]1([NH:22][C:23](=[O:15])[OH:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[CH:13]=[N:14][OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 18502Cyclohexyl isocyanate2×HCID 86026624HCID 86026624, compound

Product 1

HCID 86741958HCID 86741958, compoundYield 135.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

24 g of 3,7-dichloroquinoline-8-aldoxime were dissolved in 250 ml of dimethylformamide, 12.5 g of cyclohexyl isocyanate were added dropwise at room temperature and the solution was then stirred at 50° C. for 5 hours. In the course of the reaction period, a further 12 g of cyclohexyl isocyanate were slowly added dropwise. 2 liters of water were added to the reaction solution, and the solid was filtered off under suction, suspended in a little methanol, again filtered off under suction and recrystallized from toluene with active carbon to give 26 g (72% of theory) of 3,7-dichloroquinoline-8-aldoxime cyclohexylcarbamate of melting point 152° C.

Workup

  1. customIn the course of the reaction period
  2. filtrationthe solid was filtered off under suction
  3. filtrationagain filtered off under suction
  4. customrecrystallized from toluene with active carbon

Sources & evidence

ORD record
ord-2968cf86c29c4556ab18e9ef4bc167a4
Source dataset
uspto-grants-1988_01
Patent number
US04717416

Reaction notes

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