Methyl p-toluenesulfonate → Iodide Ion

HRID 1654980

Reaction equation

HRID 1654980 reaction equation
CC1SC2C=CC3C(C=2N=1)=CC=CC=3.[S:15]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)([O:18]C)(=[O:17])=[O:16].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[I-].[I:39]CCC[N+]1C=CC(Cl)=CC=1.C(N(CC)CC)C>C(Cl)Cl>[S:15]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)([O-:18])(=[O:17])=[O:16].[I-:39]

Participants

8

Reactant 5

HCID 6645Methyl p-toluenesulfonateHCID 8471TriethylamineHCID 75892Naphtho[1,2-d]thiazole, 2-methyl-HCID 85570p-Toluenesulfonate2×HCID 20077270HCID 20077270, compound

Product 2

HCID 30165Iodide IonHCID 85570p-Toluenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting 2,3-dimethyl-β-naphthothiazolium tosylate (Compound 7A) is prepared by heating equal moles of the 2-methyl-β-naphthothiazole (Aldrich Chemical Co.) and methyl tosylate at 160° C. for an hour. The tosylate (Compound 7A, 0.385 g, 1 mmoles) is then stirred in 10 mL of methylene chloride at room temperature with 0.41 g (1 mmoles) of 1-(3-iodopropyl)-4-chloropyridinium iodide (from 4-chloropyridine and 1,3-diiodopropane) while 0.14 mL (1 mmoles) of triethylamine is introduced. The reaction mixture is stirred at room temperature overnight and the desired monomer (Compound 7B) is isolated as its iodide salt by filtration. 7B is then dimerized according to Example 1 to yield Compound 7.

Workup

  1. additionis introduced

Sources & evidence

ORD record
ord-17aca6c6d9054603a7f74698fd84bd3f
Source dataset
uspto-grants-1995_04
Patent number
US05410030

Linked notes

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