Sodium Iodide → HCID 12852740, compound

HRID 1105883Notes

Reaction equation

HRID 1105883 reaction equation
Cl[C:2]1[S:6][N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[CH:3]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.[I-].[Na+]>C(Cl)(Cl)Cl>[N:16]1([C:2]2[S:6][N:5]([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4](=[O:15])[CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8082PiperidineHCID 8471TriethylamineHCID 13013787HCID 13013787, compound

Product 1

HCID 12852740HCID 12852740, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2.4 g. (0.01 mole) of 5-chloro-2-phenethyl-4-isothiazolin-3-one, 0.85 g. (0.01 mole) of piperidine, 1.0 g. (0.01 mole) triethylamine and 0.1 g. sodium iodide in 10 ml of CHCl3 was heated under reflux for 18 hours. The mixture was washed with water, dried (MgSO4) and concentrated to dryness to give 2.7 g. of a liquid residue. This was purified by a dry column chromatography (11/2×20", silica gel, diisopropyl ether) to give 1.0 g. of a solid product, which was recrystallized from 100 ml of diisopropyl ether to give 0.6 g of the named product, mp 106°-108°.

Workup

  1. additionA mixture of 2.4 g
  2. temperatureunder reflux for 18 hours
  3. washThe mixture was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customto give 2.7 g
  7. customThis was purified by a dry column chromatography (11/2×20", silica gel, diisopropyl ether)
  8. customto give 1.0 g
  9. customof a solid product, which was recrystallized from 100 ml of diisopropyl ether

Sources & evidence

ORD record
ord-ec43ae4e90d94b37882f57c130439013
Source dataset
uspto-grants-1982_01
Patent number
US04310590

Reaction notes

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