Methyl iodide → HCID 59852694, compound

HRID 2373455Notes

Reaction equation

HRID 2373455 reaction equation
[I: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.[Br-].[NH4+].I[CH3:16]>[OH-].[Na+].C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]([CH3:16])[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 25514Ammonium BromideHCID 178506543HCID 178506543, compound

Product 1

HCID 59852694HCID 59852694, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5-(4-iodo-phenyl)-1H-tetrazole (24) (500 mg) and ammonium bromide (1.18 g) in 1 N aq. NaOH sol. (10 ml) and CH2Cl2 (10 ml) is treated with iodomethane and vigorously stirred 26 h at RT. The organic layer is separated, washed with 1 N aq. NaOH sol., aq. NH4Cl sol. and brine. After drying over MgSO4 the solvent is evaporated and the product is purified by flash chromatography (silica gel, heptane/CH2Cl2 1:1 to pure CH2Cl2).

Workup

  1. customThe organic layer is separated
  2. washwashed with 1 N aq. NaOH sol., aq. NH4Cl sol. and brine
  3. dry with materialAfter drying over MgSO4 the solvent
  4. customis evaporated
  5. customthe product is purified by flash chromatography (silica gel, heptane/CH2Cl2 1:1 to pure CH2Cl2)

Sources & evidence

ORD record
ord-f81c87921072496e9cdaef6390406990
Source dataset
uspto-grants-2008_12
Patent number
US07459480B2

Reaction notes

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