Methyl iodide → HCID 66680950, compound

HRID 511079Notes

Reaction equation

HRID 511079 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)=[CH:4][CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]([CH3:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 178419364HCID 178419364, compound

Product 1

HCID 66680950HCID 66680950, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Bromophenyltetrazole (225 mg; 1.0 mmol) and potassium carbonate (140 mg; 1.0 mmol) are dissolved in dimethylformamide (3 mL), and a solution of methyliodide (140 mg; 1.0 mmol) in dimethylformamide (1 mL) is added dropwise under stirring. After 2 hours reaction time at room temperature methyliodide (28 mg; 0.2 mmol) is added and the mixture is stirred further for 90 minutes. The reaction is then diluted with water (4 mL), the precipitated white solid is filtered off and is rinsed once with water. After drying under high vacuum the desired product is obtained as a 95:5 mixture of regioisomers (188 mg; 0.79 mmol).

Workup

  1. additionis added
  2. stirringthe mixture is stirred further for 90 minutes
  3. filtrationthe precipitated white solid is filtered off
  4. washis rinsed once with water
  5. dry with materialAfter drying under high vacuum the desired product
  6. customis obtained as a 95:5 mixture of regioisomers (188 mg; 0.79 mmol)

Sources & evidence

ORD record
ord-c2f66da3eefc4281966731e8dbe65560
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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