Sodium Sulfide → HCID 18400155, compound

HRID 1019096Notes

Reaction equation

[N+:1]([C:4]1[C:10]([CH2:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[C:7]([CH3:16])[C:5]=1[NH2:6])([O-])=O.[S-2].[Na+].[Na+]>>[NH2:6][C:5]1[C:7]([CH3:16])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([CH2:11][CH3:12])[C:4]=1[NH2:1]

Participants

Reactant 2

HCID 14804Sodium Sulfide

HCID 12051205HCID 12051205, compound

Product 1

HCID 18400155HCID 18400155, 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-ad23d1650fd14d67b024ecaef29836b2
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486190B1

Reaction notes

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