Water → HCID 21487777, compound

HRID 1414522Notes

Reaction equation

HRID 1414522 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].O.O[N:9]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[Cl:17].S(OC)(OC)(=O)=O>O1CCOCC1>[CH:19]1([N:9]([O:4][CH3:1])[C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[Cl:17])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 21487768HCID 21487768, compound

Product 1

HCID 21487777HCID 21487777, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

20 parts of potassium carbonate in 25 parts of water is added to a solution of 16.9 parts of 2-chloronicotinic acid-N-hydroxy-N-cyclohexylamide in 50 parts of dioxane. At 45° C, 12.6 parts of dimethyl sulfate is dripped into the reaction solution and the whole stirred for 30 minutes at 45° C. The reaction product is precipitated by the addition of water. Crystallization from a mixture of benzene and ligroin yields 14.8 parts of 2-chloronicotinic acid-N-cyclohexyl-N-methoxyamide, m.p.: 96° to 98° C.

Workup

  1. customAt 45° C
  2. customThe reaction product is precipitated by the addition of water
  3. customCrystallization
  4. additionfrom a mixture of benzene and ligroin

Sources & evidence

ORD record
ord-33f89bae904a43afada2cd29db801472
Source dataset
uspto-grants-1977_01
Patent number
US04001416

Reaction notes

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