[2,6-Dinitro-4-(trifluoromethyl)phenyl]hydrazine → HCID 21541401, compound

HRID 1075893Notes

Reaction equation

HRID 1075893 reaction equation
N#N.[CH3:3][N:4]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([Cl:16])[C:10]([C:17]([F:20])([F:19])[F:18])=[CH:9][C:8]=1[NH2:21])[CH3:5].[N+]([C:25]1C=C(C(F)(F)F)C=C([N+]([O-])=O)[C:30]=1NN)([O-])=O>[Pd].C(O)C>[N+:13]([C:12]1[C:7]2[N:6]([N:4]([CH3:3])[CH3:5])[C:25]([CH3:30])=[N:21][C:8]=2[CH:9]=[C:10]([C:17]([F:18])([F:20])[F:19])[C:11]=1[Cl:16])([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 3755830[2,6-Dinitro-4-(trifluoromethyl)phenyl]hydrazineHCID 86733367HCID 86733367, compound

Product 1

HCID 21541401HCID 21541401, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.2 g. of N2 -(dimethylamino)-4-chloro-3-nitro-5-trifluoromethyl-1,2-phenylenediamine (prepared by hydrogenation of the corresponding 3,5-dinitro-4-hydrazinobenzotrifluoride in the presence of palladium catalyst) and 7.5 g. of ethyl methylcarboximidate hydrochloride in 60 ml. of ethanol was refluxed for 26 hours. The resultant 7-nitrobenzimidazole was separated by fractionation on a silica gel column, m.p. 160° - 162°C.

Workup

  1. customThe resultant 7-nitrobenzimidazole was separated by fractionation on a silica gel column, m.p. 160° - 162°C.

Sources & evidence

ORD record
ord-1fe302b1c9224647933a78857defb78c
Source dataset
uspto-grants-1976_05
Patent number
US03954788

Reaction notes

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