Benzoyl chloride → HCID 19938648, compound

HRID 36397Notes

Reaction equation

HRID 36397 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.COC1C2[C:32](=[O:34])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)SC=2C(OC)=CC=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(=O)C1C=CC=CC=1>O.CC(=O)CC>[C:32]([O:17][C:5]1[C:6]2[S:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14](=[O:16])[C:15]=2[C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:34])[C:31]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 28259241-Chloro-4-hydroxythioxanthoneHCID 125538111,4-Dimethoxythioxanthone

Product 1

HCID 19938648HCID 19938648, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-Chloro-4-hydroxythioxanthone as prepared in Example 1 (6.6 g), potassium carbonate (4.1 g), 2-butanone (60 ml) and water (6 ml) were heated under reflux. Benzoyl chloride (5.3 g) was added over 20 minutes and the mixture heated under reflux for 3 hours. A solid precipitated from solution during the heating period. The mixture was cooled, quenched with water (120 ml), the solid filtered and recrystallised from 2-butanone with a charcoal treatment. The title compound (6.8 g; 74.0%) was obtained of mp 177°-78°. Analysis C20H11ClO3S=366.81 Requires C 65.48% H 3.02% Cl 9.67% S 8.74% Found C 65.46% H 3.13% Cl 9.77% S 8.70%

Workup

  1. temperaturewere heated
  2. temperatureunder reflux
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 3 hours
  5. customA solid precipitated from solution during the heating period
  6. temperatureThe mixture was cooled
  7. customquenched with water (120 ml)
  8. filtrationthe solid filtered
  9. customrecrystallised from 2-butanone with a charcoal treatment

Sources & evidence

ORD record
ord-0b2feffbaa7645a19611e4c32927faca
Source dataset
uspto-grants-1995_05
Patent number
US05414092

Reaction notes

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