Water → Xylazine

HRID 65475

Reaction equation

HRID 65475 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]=[S:11].[NH2:12][CH2:13][CH2:14][CH2:15]O.O>CCOCC>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10]1[S:11][CH2:15][CH2:14][CH2:13][N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 90863-Amino-1-propanolHCID 879762,6-Xylyl isothiocyanate

Product 1

HCID 5707XylazineYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,6-Dimethylphenylisothiocyanate (15.0 g, 0.093 mole) was added to 3-amino-1-propanol (6.9 g, 0.093 mole) in 60 ml of ether, and the mixture was heated to reflux for 0.5 hr. After the ether was evaporated, 60 ml of concentrated hydrochloric acid was added and refluxing was continued for 0.5 hr. The cooled reaction mixture was treated with 60 ml of water and filtered. The filtrate was made basic with dilute sodium hydroxide, and the precipitate was collected by filtration and washed with water. Recrystallization from ethanol-water (charcoal) gave 16.3 g (80%) of xylazine, m.p. 136°-138° C. (lit. m.p. 140°-141° C.). This step was run three times with yields ranging from 80 to 93%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 0.5 hr
  3. customAfter the ether was evaporated
  4. addition60 ml of concentrated hydrochloric acid was added
  5. temperaturerefluxing
  6. customThe cooled reaction mixture
  7. filtrationfiltered
  8. filtrationthe precipitate was collected by filtration
  9. washwashed with water
  10. customRecrystallization from ethanol-water (charcoal)

Sources & evidence

ORD record
ord-64dc58c6a9a64c148f9a2b49232b52f6
Source dataset
uspto-grants-1986_09
Patent number
US04614798

Linked notes

Loading…