Diethyl Ether → Hydrogen Bromide

HRID 1659548Notes

Reaction equation

HRID 1659548 reaction equation
[CH2:1]([Br:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.CCOCC>C(O)C>[CH2:1]([S:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:8]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 178418431pyridine-4-thiol

Product 2

HCID 260Hydrogen BromideHCID 3182674-benzylsulfanylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of benzyl bromide (1.71 g) and 4-mercapto-pyridine (1.11 g) in ethanol (10 ml) were heated at reflux for 4 hours. Ether (5 ml) was added and the solution allowed to crystallise. Recrystallisation from ethanol-ether gave the title compound hydrobromide as a quarter hydrate (1.0 g) mp. 202°-204° C. (Found: C, 50.5; H, 4.1; N, 5.3. C12H11NS,HBr 1/4H2O requires C, 50.3; H, 4.3; N, 4.9).

Workup

  1. temperatureat reflux for 4 hours
  2. customto crystallise
  3. customRecrystallisation from ethanol-ether

Sources & evidence

ORD record
ord-1592e1546c1a45d4883cb5f2af61acb0
Source dataset
uspto-grants-1981_12
Patent number
US04304781

Reaction notes

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