Organic Syntheses Procedure

Author: Geym

Sep. 09, 2024

Organic Syntheses Procedure

Org. Synth. , 61, 14

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DOI: 10./orgsyn.061.

OXIDATION OF 5-AMINOTETRAZOLES:

BENZYL ISOCYANIDE

[

Benzene, isocyanomethyl

]

Checked by Orville L. Chapman and Thomas C. Hess.

1. Procedure

Caution! This preparation should be conducted in an

efficient hood

because of the obnoxious odor of the isocyanide.

5-Benzylaminotetrazole

. Freshly distilled

benzaldehyde

(21.2 g, 0.2 mol)

is added in one portion to a warm (50°C) solution of

5-aminotetrazole

(17.2 g, 0.2 mol)

(Note 1)

and

triethylamine

(20.2 g, 0.2 mol)

100 mL of absolute

methanol

. After 15 min the reaction mixture is cooled to room temperature, transferred to an

autoclave

, and hydrogenated with agitation at room temperature over

(10%) on

carbon

(1 g)

for 18 hr at 500 psi (pounds per square inch) of

hydrogen

. 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. Aqueous

20%

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%

), mp

183.5&#;185°C

(lit.2 mp

183°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).

Benzyl isocyanide

. In a

500-mL, round-bottomed flask

equipped with a

magnetic stirring bar

and a

pressure-equalizing funnel

are placed

5-benzylaminotetrazole

(10.5 g, 60 mmol)

100 mL of 10%

sodium hydroxide

solution, and

70 mL of

dichloromethane

. The mixture is cooled to 0°C and a solution of

NaOBr

in water (165 mL, 65 mmol)

(Note 2)

is added with vigorous stirring over a 15-min period

(Note 3)

. The

dichloromethane

layer is separated and the aqueous phase extracted with five

50-mL portions of

dichloromethane

. The combined

dichloromethane

extracts are dried over anhydrous

MgSO4

, the drying agent is removed by filtration, and the

dichloromethane

is removed by simple distillation. The pressure is then reduced to ~20 mm with an aspirator and

benzyl isocyanide

is distilled at

98&#;100°C

; yield:

5.91 g

(

84%

Boraychem supply professional and honest service.

)

(Note 4)

and

(Note 5)

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