P-Toluenesulfonylhydrazide → Methyl 2-chloro-3-(tosylhydrazono)butanoate

HRID 1721816Notes

Reaction equation

HRID 1721816 reaction equation
[Cl:1][CH:2]([C:7]([CH3:9])=O)[C:3]([O:5][CH3:6])=[O:4].[S:10]([NH:20][NH2:21])([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]>C1COCC1.CCOCC>[Cl:1][CH:2]([C:7](=[N:21][NH:20][S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:11])=[O:12])[CH3:9])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 107332Methyl 2-chloroacetoacetate

Product 1

HCID 73675184Methyl 2-chloro-3-(tosylhydrazono)butanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 25 ml of methyl 2-chloroacetoacetate in 25 ml of THF was added dropwise over 30 minutes to a solution of 37.5 g of tosyl hydrazine in 150 ml of THF. The mixture was allowed to stand overnight, then heated at reflux for 2 hours, cooled to room temperature and stripped of solvent. The residue was then dissolved in 200 ml of ether. Crystallization occurred at room temperature. The collected solids were dried to give methyl 2-chloro-3-(tosylhydrazono)butanoate (7B), as a light yellow solid, m.p.: 97°-101° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customCrystallization
  4. customoccurred at room temperature
  5. customThe collected solids were dried

Sources & evidence

ORD record
ord-fb73aa82c4234072abe40d9f77f5c2c3
Source dataset
uspto-grants-1989_08
Patent number
US04853027

Reaction notes

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