3-Phenylpropane-1-thiol → 3-Phenylpropyl 3-(1H-imidazol-4-yl)propyl sulphide

HRID 744036Notes

Reaction equation

HRID 744036 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8]Cl)[N:3]=[CH:2]1.[C:10]1([CH2:16][CH2:17][CH2:18][SH:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Na]>C(O)C>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][S:19][CH2:18][CH2:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 905963-Phenylpropane-1-thiolHCID 5360545SodiumHCID 178478458HCID 178478458, compound

Product 1

HCID 1784202743-Phenylpropyl 3-(1H-imidazol-4-yl)propyl sulphide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 mmol of 3-(1H-imidazol-4-yl)propyl chloride are introduced into a solution of 6 mmol of 3-phenylpropanethiol and 10 mmol of sodium in 30 ml of ethanol and the mixture is brought to reflux for 3 h. The suspension is evaporated under vacuum until dryness, potassium carbonate is added and the mixture is stirred in methanol/water. The residual semi-solid oil is brought to boiling in ethanol with active charcoal, filtered and recrystallized in the hydrogenmaleate form from ethanol/diethyl ether.

Workup

  1. temperatureto reflux for 3 h
  2. customThe suspension is evaporated under vacuum until dryness, potassium carbonate
  3. additionis added
  4. filtrationfiltered
  5. customrecrystallized in the hydrogenmaleate form from ethanol/diethyl ether

Sources & evidence

ORD record
ord-8f161bf4e6ed4afe9e66e59ca19f6a85
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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