Ethyl 2-(chloromethyl)-1,4-dithiaspiro[4.4]nonane-7-acetate → Ethyl 2-[(acetylthio)methyl]-1,4-dithiaspiro[4.4]nonane-7-acetate

HRID 1608270Notes

Reaction equation

HRID 1608270 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Cl[CH2:7][CH:8]1[CH2:12][S:11][C:10]2([CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]2)[S:9]1>CN(C=O)C.O>[C:1]([S:3][CH2:7][CH:8]1[CH2:12][S:11][C:10]2([CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]2)[S:9]1)(=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 19849019Ethyl 2-(chloromethyl)-1,4-dithiaspiro[4.4]nonane-7-acetateHCID 23670855Potassium ethanethioate

Product 1

HCID 19849041Ethyl 2-[(acetylthio)methyl]-1,4-dithiaspiro[4.4]nonane-7-acetateYield 103.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium thioacetate (5.4 g, 0.047 mole) and a solution of the product of Example E (4.0 g, 0.013 mole) in DMF (40 ml) was stirred under nitrogen for 2 days at room temperature. The reaction mixture was diluted with water (200 ml) and extracted twice with ethyl acetate. The organic phase was washed with brine and dried (Na2SO4). The drying agent was filtered and the filtrate stripped on the rotary evaporator to give 4.5 g of the titled compound. This material was a single spot on TLC.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe drying agent was filtered
  5. customthe filtrate stripped on the rotary evaporator

Sources & evidence

ORD record
ord-e35f119e13b94615b84063cee5bb302d
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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