Methyl iodide → HCID 53255561, compound

HRID 1460372Notes

Reaction equation

HRID 1460372 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][CH2:7][OH:8].F[C:16]1C([N+]([O-])=O)=C(O)C=CC=1.CI.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH3:16][O:8][CH2:7][CH2:6][O:5][C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([F:1])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 27827773-Fluoro-2-nitrophenolHCID 19981619HCID 19981619, compound

Product 1

HCID 53255561HCID 53255561, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

In analogous manner to that described in Preparation Example 1 Variant A a), 3g of 2-[3-fluoro-2-nitrophenoxy]ethanol were prepared from 5g of 3-fluoro-2-nitrophenol. 1.4g of the alcohol were then reacted with 7ml methyliodide with the addition of 14ml of 50% sodium hydroxide and 0.1g of the phase transfer catalyst, triethylbenzylammonium chloride. The mixture was stirred at room temperature for 2 hours. 20ml of water was then added and the product extracted into 50ml diethyl ether and the ether layer dried using magnesium sulphate. 0.8g (yield of 53%) of 3-fluoro-2-nitrophenyl (2-methoxyethyl) ether were obtained, after the solvent had been removed by evaporation, as an oil which solidified on standing. 0.8g (54% yield) of 5,7-dimethyl-2-(N-[2-fluoro-6-(2-methoxyethoxy)phenyl]-sulphamoyl)-1,2,4-triazolo[1,5-a]pyrimidine (Compound No. 11) were prepared from the ether via the 2-amino derivative in an analogous procedure to that described in Preparation Example 1, Variant A.

Workup

  1. extractionthe product extracted into 50ml diethyl ether
  2. dry with materialthe ether layer dried

Sources & evidence

ORD record
ord-a01a5b9dcb6a4984a4c42009e1d8dd5b
Source dataset
uspto-grants-1991_12
Patent number
US05071468

Reaction notes

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