Benzoyl chloride → HCID 14280410, compound

HRID 1768549Notes

Reaction equation

HRID 1768549 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[K+].[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][NH2:19])[CH3:15]>CC(C)=O.C(Cl)Cl>[C:1]([NH:12][C:11]([NH:19][CH2:18][CH2:17][N:16]([CH2:20][CH3:21])[CH2:14][CH3:15])=[S:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 60993N,N-DiethylethylenediamineHCID 516872Potassium thiocyanate

Product 1

HCID 14280410HCID 14280410, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 70 ml of benzoyl chloride in 100 ml of anhydrous acetone is added dropwise, at room temperature, to a suspension of 51 g of potassium thiocyanate in 300 ml of anhydrous acetone. When the addition is complete, the reaction mixture is refluxed for 5 minutes. A solution of 85 ml of 2-diethylaminoethylamine in 100 ml of methylene chloride is added slowly to the resulting hot solution, with vigorous stirring, so as to keep the mixture under reflux. When the addition is complete, the mixture is stirred for 1 hour at room temperature, the solvents are then evaporated off and the residue is taken up in iced water. Extraction is carried out twice with 200 ml of methylene chloride and the solution is dried over magnesium sulfate. The solvent is evaporated off to dryness and the oily product obtained is purified by chromatography on a silica column. Impurities of low polarity are removed by elution with an 80/20 (vol/vol) methylene chloride/ethyl acetate mixture. The expected product is then obtained by elution with a 95/5 (vol/vol) methylene chloride/methanol mixture.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture is refluxed for 5 minutes
  3. temperatureunder reflux
  4. additionWhen the addition
  5. customthe solvents are then evaporated off
  6. extractionExtraction
  7. dry with materialthe solution is dried over magnesium sulfate
  8. customThe solvent is evaporated off to dryness
  9. customthe oily product obtained
  10. customis purified by chromatography on a silica column
  11. customImpurities of low polarity are removed by elution with an 80/20 (vol/vol) methylene chloride/ethyl acetate mixture

Sources & evidence

ORD record
ord-070b5dae8e1d41c2934e630b620bae33
Source dataset
uspto-grants-1995_01
Patent number
US05378706

Reaction notes

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