Sodium Chloride → 6-[(2-Methoxyethoxy)methoxy]benzothiazole

HRID 1075377Notes

Reaction equation

HRID 1075377 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]Cl.[Na+].[Cl-]>CN(C)C=O>[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][O:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 1518116-Hydroxybenzothiazole

Product 1

HCID 545731596-[(2-Methoxyethoxy)methoxy]benzothiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1 g of 6-hydroxybenzothiazole in dimethyl-formamide was dropped into a solution of 0.4 g of 60% sodium hydride in 3 ml of dimethylformamide at 0° C. After the mixture was stirred at room temperature for 1 hour, 0.75 ml of (2-methoxyethoxy)methylchloride was added dropwise into the mixture and the mixture was stirred for another 1 hour. NaCl was added to the reaction mixture and the mixture was extracted with ether. The extracts were dried over sodium sulfate and concentrated, and then the residue was purified by column-chromatography (hexane : ethyl acetate=5:1) to give 0.6 g of 6-[(2-methoxyethoxy)-methoxy]benzothiazole. 1 1H-NMR(CDCl3): 3.38(s,3H), 3.58(m,2H), 3.87(m,2H), 7.22(dd,J=8.8,2.4 Hz,1H), 7.66(d,J=2.4 Hz,1H), 8.82(d,J=8.8 Hz,1H), 8.86(s,1H) IR(neat) cm-1 : 2927, 1674, 1475, 1230, 1103, 999 MS(EI) m/z: 239(M+), 89, 59

Workup

  1. stirringthe mixture was stirred for another 1 hour
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by column-chromatography (hexane : ethyl acetate=5:1)

Sources & evidence

ORD record
ord-54c2325b5476416ead32549ffe12cf2e
Source dataset
uspto-grants-1999_05
Patent number
US05900426

Reaction notes

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