Thionyl Chloride → HCID 178425258, compound

HRID 449798Notes

Reaction equation

HRID 449798 reaction equation
[CH3:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([NH:7][O:8][CH2:9][CH2:10]O)=[NH:6].S(Cl)([Cl:20])=O>O>[CH3:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([NH:7][O:8][CH2:9][CH2:10][Cl:20])=[NH:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178425259HCID 178425259, compound

Product 1

HCID 178425258HCID 178425258, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.75 g (19.9 mmol) of 3-methyl-N-(2-hydroxyethoxy)-2-nitrobenzamidine are stirred at 60° C. in 45 ml (617 mmol) of thionyl chloride for 3 h. The mixture is then cooled and carefully poured into water. The mixture is extracted with methylene chloride, the extracts are dried over sodium sulphate and the solvent is distilled off under reduced pressure. The residue is chromatographed on silica gel (cyclohexane:ethyl acetate:=4:1).

Workup

  1. temperatureThe mixture is then cooled
  2. extractionThe mixture is extracted with methylene chloride
  3. dry with materialthe extracts are dried over sodium sulphate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue is chromatographed on silica gel (cyclohexane:ethyl acetate:=4:1)

Sources & evidence

ORD record
ord-1eef8b05761b4dd99fc190b8039c83a0
Source dataset
uspto-grants-2013_07
Patent number
US08486934B2

Reaction notes

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