Benzyl mercaptan → HCID 70617393, compound

HRID 371755Notes

Reaction equation

HRID 371755 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 84.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

6.20 g of benzylmercaptan and 2 g 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 HC1 therethrough. The precipitate which forms is filtered and recrystallized in a mixture of ethyl acetate and ethanol, yielding 12.24 g 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 HC1
  6. filtrationThe precipitate which forms is filtered
  7. customrecrystallized in a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-d018e8426c0047279e7bc438128df656
Source dataset
uspto-grants-1978_05
Patent number
US04087550

Reaction notes

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