Tributylstannane → HCID 22103417, compound

HRID 1457037Notes

Reaction equation

CC1N(C(OC2C(C)=CC(C3N=NN(C)N=3)=CC=2C)CC)N=CN=1.O(C(O[CH2:35][C:36]1[N:40]([CH2:41][CH2:42][CH2:43][O:44][C:45]2[C:50]([CH3:51])=[CH:49][C:48]([C:52]3[N:53]=[N:54][N:55]([CH3:57])[N:56]=3)=[CH:47][C:46]=2[CH3:58])[N:39]=[CH:38][N:37]=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>[CH3:35][C:36]1[N:40]([CH2:41][CH2:42][CH2:43][O:44][C:45]2[C:46]([CH3:58])=[CH:47][C:48]([C:52]3[N:53]=[N:54][N:55]([CH3:57])[N:56]=3)=[CH:49][C:50]=2[CH3:51])[N:39]=[CH:38][N:37]=1

Participants

Conditions

Temperature: 75 °C

Procedure

5-Methyl-1-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]3-propyl]-1,2,4-triazole (I, Azo=5-methyl-1,2,4-triazol-1-yl, Y=1,3-propylene, R1,R2 =3,5-dimethyl, R3 =2-methyl-tetrazol-5-yl) p 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

concentrationThe solvent was concentrated in vacuo
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-d1ae866b964145fe962eefec752b3639
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05846986

Reaction notes

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