Dibutyltin oxide → HCID 178424895, compound

HRID 1386488Notes

Reaction equation

C([Sn](=O)CCCC)CCC.C[Si]([N:15]=[N+:16]=[N-:17])(C)C.[F:18][C:19]([F:45])([F:44])[C:20]([C:36]1[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=1)=[CH:21][C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=2[CH:23]=1>C1(C)C=CC=CC=1>[F:18][C:19]([F:44])([F:45])[C:20]([C:36]1[CH:43]=[CH:42][C:39]([C:40]2[NH:41][N:17]=[N:16][N:15]=2)=[CH:38][CH:37]=1)=[CH:21][C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=2[CH:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Dibutyl tin oxide (15.1 mg, 10% mol) and trimethylsilyl azide (0.16 ml, 1.22 mmol), are added successively to a solution of the (E) compound 4-[1-trifluoromethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-ethenyl]benzonitrile (0.24 g, 0.61 mmol) in anhydrous toluene (1.25 ml). The reaction medium is heated for 16 hours at reflux (110° C.) under an atmosphere of argon and with magnetic stirring. The mixture is purified by flash chromatography on silica (eluent CH2Cl2 then MeOH:CH2Cl2=5:95) to obtain, after evaporation and washing with pentane, a greenish powder, compound (E) 5-[4-[1-trifluoromethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-ethenyl]phenyl]-1H-tetrazole (compound CB77402) (yield=58%), which is dried at 50° C. (24 hours) in a desiccator. This solid can be recrystallised with chloroform.

Workup

temperatureThe reaction medium is heated for 16 hours
customThe mixture is purified by flash chromatography on silica (eluent CH2Cl2
customMeOH:CH2Cl2=5:95) to obtain
customafter evaporation
washwashing with pentane

Sources & evidence

ORD record: ord-e078ceb49847486bbf3a0450eecf5ad0
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265423B1

Reaction notes

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