Thionyl Chloride → Hydrochloric Acid

HRID 2107561Notes

Reaction equation

HRID 2107561 reaction equation
[ClH:1].[NH2:2][C:3]1[S:4][C:5]([CH2:8][CH2:9]O)=[CH:6][N:7]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[Cl:13][CH2:9][CH2:8][C:5]1[S:4][C:3]([NH2:2])=[N:7][CH:6]=1.[ClH:1]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 13637185HCID 13637185, compound

Product 2

HCID 313Hydrochloric AcidHCID 13637165HCID 13637165, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 14.73 g of 2-amino-5-thiazoleethanol, monohydrochloride (Example B) in 200 ml of chloroform is added rapidly 50 ml of thionyl chloride. The mixture is refluxed for 30 minutes, cooled to room temperature, filtered through a pad of Celite, concentrated to a brown oily solid, and crystallized from ethanol-diethyl ether to give 5-(2-chloroethyl)-2-thiazolamine as the monohydrochloride salt; mp 145°-147° C.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. filtrationfiltered through a pad of Celite
  3. concentrationconcentrated to a brown oily solid
  4. customcrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-6aebfb8c3fb54e01809982eee3d0d338
Source dataset
uspto-grants-1990_06
Patent number
US04935424

Reaction notes

Loading…