1-Bromopropane → 9H-Thioxanthen-9-one, 1-chloro-4-propoxy-

HRID 36395Notes

Reaction equation

HRID 36395 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][CH2:25][CH2:26]Br>CC(C)=O>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([O:17][CH2:24][CH2:25][CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 28259241-Chloro-4-hydroxythioxanthone

Product 1

HCID 52128569H-Thioxanthen-9-one, 1-chloro-4-propoxy-Yield 75.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Chloro-4-hydroxythioxanthone (7.8 g; 0.03 mol) prepared as above and potassium carbonate (5.0 g; 0.036 mol) was stirred and refluxed for 10 minutes in acetone (50 ml). n-Propyl bromide (5.5 g; 0.045 mol) was added and the resulting mixture heated under reflux for 16 hours. The mixture was then cooled and quenched on to water (250 ml). The solid was filtered and washed with water the resulting damp solid recrystallised from ethanol (50 ml) to afford the title compound (6.9 g; 75.5%) of mp 102°-3°. Analysis C16H13ClO2S=304.777 Requires C 63.05%; H 4.30%; Cl 11.63%; S 10.52% Found C 63.14%; H 4.37%; Cl 11.66%; S 10.63%

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 16 hours
  3. temperatureThe mixture was then cooled
  4. customquenched on to water (250 ml)
  5. filtrationThe solid was filtered
  6. washwashed with water the resulting damp solid
  7. customrecrystallised from ethanol (50 ml)

Sources & evidence

ORD record
ord-9f9292b5befb4595a3e0f33675685eb0
Source dataset
uspto-grants-1995_05
Patent number
US05414092

Reaction notes

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