Sodium Acetate → HCID 14452902, compound

HRID 2165259Notes

Reaction equation

HRID 2165259 reaction equation
[NH2:1][C:2]1[C:3]([Cl:11])=[N:4][C:5]([CH2:9][CH3:10])=[CH:6][C:7]=1[Cl:8].[C:12]([O-])(=[O:14])[CH3:13].[Na+]>C(OC(=O)C)(=O)C>[C:12]([NH:1][C:2]1[C:3]([Cl:11])=[N:4][C:5]([CH2:9][CH3:10])=[CH:6][C:7]=1[Cl:8])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 14452901HCID 14452901, compound

Product 1

HCID 14452902HCID 14452902, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

7.8 g (40.8 mmol) of 3-amino-2,4-dichloro-6-ethyl-pyridine are heated under reflux for two hours in a mixture of 40 ml of acetic anhydride and 4 g (49 mmol) of anhydrous sodium acetate. The mixture is subsequently evaporated in vacuo, the residue is partitioned between dilute NH3 solution and CHCl3, and the organic phase is separated off, dried using Na2SO4 and evaporated. The residue (11.2 g) consists of a mixture of mono- and diacetylated amine. It is dissolved in 50 ml of methanol, 10 g of powdered K2CO3 are added and the mixture is stirred for one hour at room temperature. It is subsequently evaporated and partitioned between water and CHCl3, and the organic phase is separated off and washed with 5% strength aqueous NaH2PO4 solution. After drying using Na2SO4, the organic phase is evaporated. The residue is stirred with ether and filtered off with suction. Yield 7.7 g (80.9% of theory) melting point: 142° C.

Workup

  1. customThe mixture is subsequently evaporated in vacuo
  2. customthe residue is partitioned between dilute NH3 solution and CHCl3
  3. customthe organic phase is separated off
  4. customdried
  5. customevaporated
  6. additionThe residue (11.2 g) consists of a mixture of mono- and diacetylated amine
  7. dissolutionIt is dissolved in 50 ml of methanol
  8. addition10 g of powdered K2CO3 are added
  9. customIt is subsequently evaporated
  10. custompartitioned between water and CHCl3
  11. customthe organic phase is separated off
  12. washwashed with 5% strength aqueous NaH2PO4 solution
  13. customAfter drying
  14. customthe organic phase is evaporated
  15. stirringThe residue is stirred with ether
  16. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-15bc2417e70f4dca9ca997e23f114d65
Source dataset
uspto-grants-1990_07
Patent number
US04939262

Reaction notes

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