Tetrafluoroboric acid → HCID 18400152, compound

HRID 1019097Notes

Reaction equation

[N+](=[C:3]1[N:7]=[C:6]2[C:8]([CH3:17])=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[C:11]([CH2:12][CH3:13])[C:5]2=[N:4]1)=[N-].N([O-])=O.[Na+].[F:22][B-](F)(F)F.[H+]>>[CH2:12]([C:11]1[C:5]2[NH:4][C:3]([F:22])=[N:7][C:6]=2[C:8]([CH3:17])=[CH:9][C:10]=1[N+:14]([O-:16])=[O:15])[CH3:13]

Participants

Reactant 3

HCID 28118Tetrafluoroboric acid

HCID 23668193Sodium Nitrite

HCID 86758619HCID 86758619, compound

Product 1

HCID 18400152HCID 18400152, compound

Procedure

2,4-Dinitro-3-ethyl-6-methylaniline (see Example 2) is treated with sodium sulfide to afford 1,2-diamino-3-ethyl-6-methyl-4-nitrobenzene. Treatment with cyanogen bromide affords to 2-amino-4-ethyl-7-methyl-5-nitrobenzimidazole. This is converted to 2-diazo-4-ethyl-7-methyl-5-nitrobenzimidazole tetrafuoroborate with sodium nitrite and tetrafluoroboric acid. Thermal decomposition of the diazonium salt gives 4-ethyl-2-fluoro-7-methyl-5-nitrobenzimidazole. Conversion to 4-ethyl-2-fluoro-5-(2-imidazolinylamino)benzimidazole is completed according to Scheme 5.

Sources & evidence

ORD record: ord-62e887964ad54d1c95f53c60613ebd92
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486190B1

Reaction notes

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