Dichloroacetaldehyde → 2,2-Dichloroacetaldehyde tosylhydrazone

HRID 352061Notes

Reaction equation

HRID 352061 reaction equation
[S:1]([NH:11][NH2:12])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:13][CH:14]([Cl:17])[CH:15]=O>C(O)(=O)CC>[S:1]([NH:11][N:12]=[CH:15][CH:14]([Cl:17])[Cl:13])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 6576DichloroacetaldehydeHCID 15303P-Toluenesulfonylhydrazide

Product 1

HCID 671758942,2-Dichloroacetaldehyde tosylhydrazoneYield 70%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

Tosylhydrazine (234 g, 1.26 mol) was suspended in propionic acid (2 L) and dichloroacetaldehyde (142 g, 1.26 mol) was added at 15-20° C. The mixture was stirred at room temperature for 2 hours and under ice-cooling for 3 hours. The precipitated crystals were collected by filtration and washed with toluene. The crystals were dried under reduced pressure to give 2,2-dichloroacetaldehyde tosylhydrazone (247 g, yield 70%).

Workup

  1. temperaturecooling for 3 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with toluene
  4. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-15bbb390251345f0a7952e3d8da65690
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

Loading…