Methyl iodide → HCID 22723445, compound

HRID 1272203Notes

Reaction equation

HRID 1272203 reaction equation
[N:1]1[CH:5]=[N:4][N:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[N:2]=1.[OH-].[Na+].I[CH3:16]>CN(C)C=O.O.C(OCC)(=O)C>[CH3:16][N:1]1[CH:5]=[N:4][N:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[NH:2]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 22723466HCID 22723466, compound

Product 1

HCID 22723445HCID 22723445, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Tetrazol-3-yl)phenol (32.8 g, 202.3 mmol) is dissolved in dimethylformamide (100 mL) and water (25 mL) and cooled in ice. Sodium hydroxide (8.49 g, 212.3 mmol) in water (20 mL) is added and the solution is warmed to ambient temperature. After thirty minutes, iodomethane (31.58 g, 222.5 mmol) is added neat. The solution is stirred for 15 hours then diluted with ethyl acetate (300 mL) and water (500 mL). The aqueous layer is washed three times with ethyl acetate (300 mL) and the organic layers are combined, washed three times with water (1 L), once with brine (1.2 L), dried over magnesium sulfate, filtered and concentrated in vacuo. The solid is purified by flash column chromatography (80% hexane:20% ethyl acetate gradient to 50% hexane:50% ethyl acetate as an eluent) to give 23.5 g of 2-(1-methyltetrazol-3-yl)phenol (66%).

Workup

  1. waitAfter thirty minutes
  2. washThe aqueous layer is washed three times with ethyl acetate (300 mL)
  3. washwashed three times with water (1 L)
  4. dry with materialonce with brine (1.2 L), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe solid is purified by flash column chromatography (80% hexane

Sources & evidence

ORD record
ord-c00fe1f5fb6a4510a97e4ae1bae33c27
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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