Sodium Hydroxide → HCID 178420452, compound

HRID 1284491Notes

Reaction equation

[C:1]([CH2:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[N:5]=1)#[N:2].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O.O>[C:9]1([N:8]2[C:7]3[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=3[N:5]=[C:4]2[CH2:3][C:1]2[NH:21][N:20]=[N:19][N:2]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-cyanomethyl-1-phenyl-1H-benzimidazole (6.2 g), sodium azide (5.18 g) and ammonium chloride (4.27 g) in N,N-dimethylformamide (62 ml) was heated at 100° C. for 4 hours. The reaction mixture was poured into water (620 ml) and the aqueous mixture was adjusted to pH 9 with 1 N sodium hydroxide. After being washed with ethyl acetate, the aqueous layer was further adjusted to pH 4 with acetic acid and extracted twice with ethyl acetate. The combined extract was washed with water and saturated sodium chloride in turn and dried over magnesium sulfate. The solvent was removed under reduced pressure to give a residue, which was recrystallized from a mixture of methanol and diisopropyl ether to give 5-(1-phenyl-1H-benzimidazol-2-yl)methyl-1H-tetrazole (5.3 g).

Workup

washAfter being washed with ethyl acetate
extractionextracted twice with ethyl acetate
extractionThe combined extract
washwas washed with water and saturated sodium chloride in turn
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customto give a residue, which
customwas recrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record: ord-c1fbbcaa61a74eb9bd8d212a9278071f
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04563455

Reaction notes

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