Acetic Acid → HCID 178456787, compound

HRID 1089443Notes

Reaction equation

HRID 1089443 reaction equation
[H-].[Na+].[C:3]([CH:5]([CH3:13])[C:6](OC(C)(C)C)=O)#[N:4].Cl[C:15]1[N:16]=[N:17]C(Cl)=[CH:19][CH:20]=1.C(O)(=[O:24])C>O1CCCC1>[OH:24][C:15]1[N:16]=[N:17][C:6]([CH:5]([CH3:13])[C:3]#[N:4])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 14919492Tert-butyl 2-cyano-2-methylacetate

Product 1

HCID 178456787HCID 178456787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60.4 g (2.02 mol) of 80% strength sodium hydride in white oil are suspended in 2 liters of tetrahydrofuran and 311.8 g (2.02 mol) of tert.-butyl 2-cyanopropionate are added dropwise at 20°-30° C. During the course of 45 minutes this clear solution is added dropwise to a solution of 298 g (2.0 mol) of 3,6-dichloropyridazine and the mixture is heated under reflux for 2 hours. 317 ml of acetic acid are then added and the solvent is removed in vacuo. The residue is taken up in a mixture of 6,400 ml of acetic acid, 250 ml of acetic anhydride and 32 g of p-toluenesulfonic acid monohydrate, heated under reflux for 3 hours and again brought to dryness in vacuo. The residue is suspended in a little water, adjusted to pH 5 with sodium hydroxide solution and the water removed by evaporation. The residue is extracted hot using ethyl acetate. 99.7 g (33% of theory) of crude product are thus obtained, which can be employed for the following reaction without further processing.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent is removed in vacuo
  4. additionThe residue is taken up in a mixture of 6,400 ml of acetic acid, 250 ml of acetic anhydride and 32 g of p-toluenesulfonic acid monohydrate
  5. temperatureheated
  6. temperatureunder reflux for 3 hours
  7. customthe water removed by evaporation
  8. extractionThe residue is extracted hot
  9. custom99.7 g (33% of theory) of crude product are thus obtained
  10. customwhich can be employed for the following reaction without further processing

Sources & evidence

ORD record
ord-f796673195304f088d5b5eb889344b33
Source dataset
uspto-grants-1990_10
Patent number
US04966902

Reaction notes

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