1,2-Dimethoxyethane → HCID 23368329, compound

HRID 1901548Notes

Reaction equation

HRID 1901548 reaction equation
C[C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9]([CH3:12])(=O)=O)[S:4][N:3]=1.[SH-].[K+].[CH2:15]([O:18]CCl)[C:16]#[CH:17].[CH2:21](COC)[O:22]C>O>[CH3:21][O:22][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH2:12][O:18][CH2:15][C:16]#[CH:17])[S:4][N:3]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 102109Potassium bisulfideHCID 122413411-Propyne, 3-(chloromethoxy)-HCID 23368334HCID 23368334, compound

Product 1

HCID 23368329HCID 23368329, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.18 Grams of 3-methyl-4-cyano-5-methylsulfonylisothiazole was dissolved in 20 ml of dimethoxyethane, and a solution of 1.2 g of potassium hydrosulfide (KSH) in 5 ml of water was added at room temperature with stirring. After stirring for 10 minutes, 1.3 g of 2-propynyloxymethyl chloride was added, and the reaction solution was stirred for 3 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extract was washed with water, dried and concentrated to obtain 2.1 g of an oily 3-methoxy-4-cyano-5-(2-propynyloxymethylthio)isothiazole. This product was dissolved in 20 ml of DMF and ice-cooled to 5° to 10° C. To this solution was added a solution of 5.1 g of iodine and 3.2 g of potassium iodide in 5 ml of water and 10 ml of DMF, and then 6.6 g of a 10% KOH was added dropwise. After addition, the reaction solution was stirred for 2 hours until the temperature reached room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure to obtain an oily product. This product was recrystallized from ether to obtain 2.7 g of white crystals having a melting point of 124° to 125° C. (yield 76%).

Workup

  1. stirringAfter stirring for 10 minutes
  2. stirringthe reaction solution was stirred for 3 hours
  3. extractionwas then extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ab8d0a591e34ba287dbb51bc93a52ce
Source dataset
uspto-grants-1996_11
Patent number
US05578622

Reaction notes

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