Ethanol → HCID 15462098, compound

HRID 460765Notes

Reaction equation

HRID 460765 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8](Br)[CH2:9][CH2:10][Cl:11])=O)=[CH:4][CH:3]=1.[S-:15][C:16]#[N:17].[K+].C([OH:21])C>O>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]2[NH:17][C:16](=[O:21])[S:15][C:8]=2[CH2:9][CH2:10][Cl:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 516872Potassium thiocyanateHCID 30165872-Bromo-4-chloro-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 15462098HCID 15462098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-p-fluorophenyl-5-β-chloroethyl-4-thiazolin-2-one is prepared in the following manner: A mixture of 30 g of 1-p-fluorobenzoyl-1-bromo-3-chloropropane (prepared in accordance with our Italian Patent Application No. 23444 A/72 filed 22.4.1972), 11.5 g of potassium thiocyanate, 120 cc of ethanol and 6 cc of water is boiled under reflux for 4 hours. The precipitated solid is filtered while hot and 1-p-fluorobenzoyl-1-thiocyano-3-chloropropane precipitates from the filtrate on cooling. 22.1 g of the latter, 66 cc of glacial acetic acid and 11 cc of concentrated H2SO4 are boiled under relux for 4 hours. The acetic acid is removed from the reacting mass under reduced pressure and the residue is extracted while hot with chloroform. The chloroform solution is evaporated to dryness under reduced pressure and the residue recrystallised. M.P. = 138° C (from isopropyl alcohol).

Workup

  1. customprepared in accordance with our Italian Patent Application No
  2. temperatureunder reflux for 4 hours
  3. filtrationThe precipitated solid is filtered while hot and 1-p-fluorobenzoyl-1-thiocyano-3-chloropropane
  4. customprecipitates from the filtrate
  5. temperatureon cooling
  6. customThe acetic acid is removed from the reacting mass under reduced pressure
  7. extractionthe residue is extracted while hot with chloroform
  8. customThe chloroform solution is evaporated to dryness under reduced pressure
  9. customthe residue recrystallised

Sources & evidence

ORD record
ord-40744703f82e456f9aea27aaa3296dbb
Source dataset
uspto-grants-1977_12
Patent number
US04061637

Reaction notes

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