Azobisisobutyronitrile → HCID 22103390, compound

HRID 741648Notes

Reaction equation

HRID 741648 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:33]=[C:32]([CH3:34])[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH:15]([C:26]3[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=3)OC(OC3C=CC=CC=3)=S)=[C:9]([CH3:35])[CH:8]=2)=[N:3]1.CC(N=NC(C#N)(C)C)(C#N)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:33]=[C:32]([CH3:34])[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:26]3[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=3)=[C:9]([CH3:35])[CH:8]=2)=[N:3]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 516892Sodium BicarbonateHCID 19426779HCID 19426779, compound

Product 1

HCID 22103390HCID 22103390, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-1-phenoxythiocarbonyloxy-butyl]-1-methylimidazole (1.94 mmol) in 35 ml of toluene was added AIBN (159 mg, 0.97 mmol) and n-tributyltin hydride (1.69 g), and the mixture was stirred at 75°-80° C. for 4 h. An aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate, and then methylene chloride (2×). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (20 cm column, methylene chloride/methanol, 30/1-15/1) to afford 440 mg (67%) of 2-[4-[4-(2-methyltetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-1-methylimidazole, m.p. 100°-102° C. (from methylene chloride/hexane).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica column chromatography (20 cm column, methylene chloride/methanol, 30/1-15/1)

Sources & evidence

ORD record
ord-6e713fbb0a0b4e268ab6fcef1a749f6c
Source dataset
uspto-grants-1996_09
Patent number
US05552420

Reaction notes

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