Water → HCID 22416982, compound

HRID 1721035Notes

Reaction equation

HRID 1721035 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([OH:7])[CH:3]=1.[H-].[Na+].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:13]=1[CH2:14]Cl.O>CN(C)C=O>[Cl:1][C:2]1[S:6][N:5]=[C:4]([O:7][CH2:14][C:13]2[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:12]=2[O:11][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2911942,5-Dimethoxybenzyl chlorideHCID 178516207HCID 178516207, compound

Product 1

HCID 22416982HCID 22416982, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5-chloro-3-hydroxyisothiazole (4.0 g, 0.03 mole) in 15 ml of dimethyl formamide was added dropwise to a stirred suspension of 60% NaH in oil (1.4 g, 0.035 mole) in 25 ml of dimethyl formamide at 0° C. under N2. After 15 minutes, a solution of 2,5-dimethoxybenzyl chloride (5.6 g, 0.03 mole) in 10 ml of dimethyl formamide was added dropwise and the mixture was stirred at room temperature for 24 hours. The dark reaction mixture was poured into water and extracted with diethyl ether. The diethyl ether extract was washed with water, dried (MgSO4), and concentrated. The residual white solid was purified by column chromatography on silica gel, using diethyl ether/hexane (1/1) as eluant. 5-Chloro-3-(2,5-dimethoxybenzyloxy)isothiazole was obtained as a white solid; 4.7 g; mp 52°-55° C.

Workup

  1. customThe dark reaction mixture
  2. extractionextracted with diethyl ether
  3. extractionThe diethyl ether extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residual white solid was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e18ddf1a83314c3bb6331252a8422c18
Source dataset
uspto-grants-1996_04
Patent number
US05508417

Reaction notes

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