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Read MoreOrg. Synth. , 61, 14
DOI: 10./orgsyn.061.
OXIDATION OF 5-AMINOTETRAZOLES:
BENZYL ISOCYANIDE
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[
Benzene, isocyanomethyl
]1. Procedure
Caution! This preparation should be conducted in an
efficient hood
because of the obnoxious odor of the isocyanide.5-Benzylaminotetrazole
. Freshly distilledbenzaldehyde
(21.2 g, 0.2 mol) is added in one portion to a warm (50°C) solution of5-aminotetrazole
(17.2 g, 0.2 mol)(Note 1)
andtriethylamine
(20.2 g, 0.2 mol) in100 mL of absolute
methanol
. After 15 min the reaction mixture is cooled to room temperature, transferred to anautoclave
, and hydrogenated with agitation at room temperature overPd
(10%) oncarbon
(1 g) for 18 hr at 500 psi (pounds per square inch) ofhydrogen
. The catalyst is removed by filtration and all volatile material is removed at 60°C under aspirator pressure. The gummy tan solid is triturated with 250 mL of hot water. Aqueous20%
HCl
is added until pH 3 is reached. The mixture is cooled to room temperature and the solid collected, washed with water, and dried over-night at room temperature under reduced pressure (100 μ); yield:27.5 g
(80%
), mp183.5&#;185°C
(lit.2 mp183°C
).A.. Freshly distilledis added in one portion to a warm (50°C) solution ofandin. After 15 min the reaction mixture is cooled to room temperature, transferred to an, and hydrogenated with agitation at room temperature overfor 18 hr at 500 psi (pounds per square inch) of. The catalyst is removed by filtration and all volatile material is removed at 60°C under aspirator pressure. The gummy tan solid is triturated with 250 mL of hot water. Aqueousis added until pH 3 is reached. The mixture is cooled to room temperature and the solid collected, washed with water, and dried over-night at room temperature under reduced pressure (100 μ); yield:), mp(lit.mp).
B.
Benzyl isocyanide
. In a500-mL, round-bottomed flask
equipped with amagnetic stirring bar
and apressure-equalizing funnel
are placed5-benzylaminotetrazole
(10.5 g, 60 mmol),100 mL of 10%
sodium hydroxide
solution, and70 mL of
dichloromethane
. The mixture is cooled to 0°C and a solution ofNaOBr
in water (165 mL, 65 mmol)(Note 2)
is added with vigorous stirring over a 15-min period(Note 3)
. Thedichloromethane
layer is separated and the aqueous phase extracted with five50-mL portions of
dichloromethane
. The combineddichloromethane
extracts are dried over anhydrousMgSO4
, the drying agent is removed by filtration, and thedichloromethane
is removed by simple distillation. The pressure is then reduced to ~20 mm with an aspirator andbenzyl isocyanide
is distilled at98&#;100°C
; yield:5.91 g
(84%
)(Note 4)
and(Note 5)
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