Thionyl Chloride → HCID 178425258, compound

HRID 558070Notes

Reaction equation

HRID 558070 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-2006aa7f11e8483ba19cb520b0fe892c
Source dataset
uspto-grants-2011_11
Patent number
US08062995B2

Reaction notes

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