Thionyl Chloride → HCID 54424951, compound

HRID 259622Notes

Reaction equation

HRID 259622 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](O)=[O:12])=[CH:7][C:6]=1[Cl:16])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[N-:21]=[N+:22]=[N-:23].[Na+]>C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([N:21]=[N+:22]=[N-:23])=[O:12])=[CH:7][C:6]=1[Cl:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 54169306HCID 54169306, compound

Product 1

HCID 54424951HCID 54424951, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

24.0 g (0.1 mol) of 4-acetoxy-3-chloro-cinnamic acid are suspended in 90 ml of benzene and 14.6 ml (0.2 mol) of thionyl chloride are added. The reaction mixture is heated to the boil for half an hour under a reflux condenser and thereafter the solvent and excess thionyl chloride are removed by distillation under reduced pressure. The residual crude 4-acetoxy-3-chloro-cinnamic acid chloride is dissolved in 100 ml of absolute 1,2-dimethoxyethane, 19.5 g (0.3 mol) of sodium azide are added and thereafter the mixture is stirred for 48 hours at room temperature. The inorganic salts are then filtered off and the filtrate is concentrated under reduced pressure at 30° C. Hereupon, colourless crystals separate out. The crystallisation is completed by adding ether. 4-Acetoxy-3-chloro-cinnamic acid azide of melting point 102°-103° C. (decomposition) is thus obtained.

Workup

  1. temperatureThe reaction mixture is heated to the boil for half an hour under a reflux condenser
  2. customthe solvent and excess thionyl chloride are removed by distillation under reduced pressure
  3. dissolutionThe residual crude 4-acetoxy-3-chloro-cinnamic acid chloride is dissolved in 100 ml of absolute 1,2-dimethoxyethane
  4. filtrationThe inorganic salts are then filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure at 30° C
  6. customHereupon, colourless crystals separate out
  7. customThe crystallisation
  8. additionby adding ether

Sources & evidence

ORD record
ord-c35e80e67e50404d88019658141eebba
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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