Tributylstannane → HCID 22103417, compound

HRID 741661Notes

Reaction equation

HRID 741661 reaction equation
O(C(O[CH2:11][C:12]1[N:16]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([CH3:27])=[CH:25][C:24]([C:28]3[N:29]=[N:30][N:31]([CH3:33])[N:32]=3)=[CH:23][C:22]=2[CH3:34])[N:15]=[CH:14][N:13]=1)=S)C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:11][C:12]1[N:16]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:22]([CH3:34])=[CH:23][C:24]([C:28]3[N:29]=[N:30][N:31]([CH3:33])[N:32]=3)=[CH:25][C:26]=2[CH3:27])[N:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 54310283HCID 54310283, compound

Product 1

HCID 22103417HCID 22103417, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-phenoxythiocarbonyloxymethyl-1-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole (130 mg, 0.79 mmol) in 20 ml of toluene was added AIBN (130 mg, 0.79 mmol) and tributyltin hydride (3.2 g, 11 mmol) and the mixture was stirred at 75° C. for 6.5 h. The solvent was concentrated in vacuo and the residue was purified by silica column chromatography (13 cm column, ethyl acetate/hexane, 1/1-5/1; methylene chloride/acetone, 4/1-0/1) to afford 61 mg (19%) of 5-methyl-1-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole, m.p. 126°-128° C.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was purified by silica column chromatography (13 cm column, ethyl acetate/hexane, 1/1-5/1; methylene chloride/acetone, 4/1-0/1)

Sources & evidence

ORD record
ord-a12d34acf06a44c4b81b2806abd149ba
Source dataset
uspto-grants-1996_09
Patent number
US05552420

Reaction notes

Loading…