Thionyl Chloride → 2-(4-Amino-2-methylphenyl)-1,3-propanediol sulphite

HRID 484635Notes

Reaction equation

HRID 484635 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][OH:12])[CH2:9][OH:10])=[C:4]([CH3:13])[CH:3]=1.[S:14](Cl)(Cl)=[O:15].ClCCl.[O:21]1CCOCC1>>[S:14]([O:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=1[CH3:13])[CH2:11][OH:12])([OH:15])=[O:21]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 18626912Dioxane methylene chlorideHCID 202715922-(4-Amino-2-methylphenyl)propane-1,3-diol

Product 1

HCID 1317142902-(4-Amino-2-methylphenyl)-1,3-propanediol sulphiteYield 90%

Procedure

(c') 2-(4-Amino-2-methylphenyl)-1,3-propanediol (0.8 g; 4.4 mmol) was taken up in dichloromethane/dioxane (1/1; 20 ml), and thionylchloride (1.6 g; 13.2 mmol) was added over 30 minutes, at room temperature. The solution was heated under reflux with stirring for an additional hour. The solvent was evaporated, the residue was neutralized with a NaHCO3 solution in water and the aqueous solution was thoroughly extracted with dichloromethane. The organic layers were dried over MgSO4 and evaporated to dryness. The remaining oil (0.9 g) consisted of 2-(4-amino-2-methylphenyl)-1,3-propanediol sulphite (yield 90%, purity >90%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. customThe solvent was evaporated
  4. extractionthe aqueous solution was thoroughly extracted with dichloromethane
  5. dry with materialThe organic layers were dried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-50c55a4f408c483b9d6c20010d673669
Source dataset
uspto-grants-1985_08
Patent number
US04533379

Reaction notes

Loading…