Benzyl mercaptan → HCID 70617393, compound

HRID 917973Notes

Reaction equation

HRID 917973 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl-:11].[CH2:12]([N+:14]1([CH2:19][CH3:20])[CH2:17][CH:16]([OH:18])[CH2:15]1)[CH3:13]>O.C(O)C.CCOCC>[ClH:11].[CH2:1]([S:8][CH2:17][CH:16]([OH:18])[CH2:15][N:14]([CH2:19][CH3:20])[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 11389597Azetidinium, 1,1-diethyl-3-hydroxy-, chloride

Product 1

HCID 70617393HCID 70617393, compoundYield 84.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

6.20 g of benzylmercaptan and 2g of NaOH are stirred together in 25 cc of water, under a nitrogen atmosphere, for 5 minutes at which time there is added thereto a solution of 8.28 g of 1,1-diethyl-3-hydroxy azetidinium chloride in 25 cc of ethyl alcohol. The resulting mixture is heated for 1 hour at 75°C. After evaporating to dryness the product thus obtained is taken up in ether. The resulting etherified solution is then dried on sodium sulfate and neutralized by bubbling gaseous HCl therethrough. The precipitate which forms is filtered and recrystallized in a mixture of ethyl acetate and ethanol, yielding 12.25g of white crystals melting at 104°C

Workup

  1. additionis added
  2. customAfter evaporating to dryness the product
  3. customthus obtained
  4. customThe resulting etherified solution is then dried on sodium sulfate
  5. customby bubbling gaseous HCl
  6. filtrationThe precipitate which forms is filtered
  7. customrecrystallized in a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-4040ccf337134c298de4a3074b14c4b6
Source dataset
uspto-grants-1976_07
Patent number
US03968218

Reaction notes

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